Vacation Home Rentals By Owner In Great Barrington, MA

$648.95

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington, Massachusetts, United States

Experience the charm of country living year-round on 4+ acres of peaceful land, tucked away on a private lane just minutes from Downtown Great Barrington and Tanglewood. brbrThis inviting home offers seamless indoor-outdoor living with abundant natural light, a spacious 1,000+ square foot deck, expansive yard, vibrant gardens, and a relaxing outdoor hot tub. Perfect for families, groups of friends, and even your well-behaved pup, this Berkshires retreat is a one-of-a-kind getaway.brbrWelcome to your home away from home in the heart of the Berkshires—where comfort meets adventure. This spacious retreat is perfectly located just a short, scenic drive from some of the region’s most beloved destinations:brbr- Great Barrington/Stockbridge/Lenox for shopping, dining, and culturebr- Tanglewood and Jacob’s Pillow for unique live performancesbr- Norman Rockwell Museum, The Clark, and Mass MoCA for world-class artbr- Lakes, rivers, trails, and nature preserves for outdoor lovers of all kindsbrbrAfter a day of exploring, gather in the chef’s kitchen—a true standout of the home. Outfitted with premium appliances including a Thermador induction stove, KitchenAid dual oven, Liebherr fridge/freezer, wine fridge, Chemex and electric coffeemakers, and All-Clad pots/pans, it’s fully stocked with everything you need to cook and serve memorable meals. The countertops—crafted from Vermont Danby marble and soapstone—are as elegant as they are functional.brbrStep right outside from the kitchen to a 1,000+ square foot deck surrounded by lush grapevines, hummingbirds, and peaceful woods. Enjoy morning coffee in the sun, dinner al fresco at the large dining table, or a soak in the outdoor hot tub under the stars. There's also a gas grill, fire pit, lounge seating, and a generous yard for games or relaxing.brbrEach floor has its own full bathroom for maximum privacy and convenience.brbrSleeping arrangements:brbrThis home sleeps up to 8 guests across 4 bedrooms, with 3 full bathrooms and 1 half bath:brbr- Main level primary suite: King bed with en suite bathroom (tub + shower)brbr- Upstairs Bedroom 1: Queen bedbrbr- Upstairs Bedroom 2: Two twin bedsbrbr- Lower level Bedroom: Full bedbrbrOther highlights include:brbr- Central A/Cbr- Cozy wood-burning fireplace in the living roombr- Smart TVs in the living room and upstairs bedroom (stream Netflix, Hulu, Prime, etc.)br- Dining table for 10 + kitchen island seating for 4br- Rapid ice maker on top of the beverage fridge (freezer ice maker is off)br- Washer/dryer, hotel-quality linens and towelsbr- Stocked with shampoo, conditioner, and body washbr- Parking for 4–6 cars across two drivewaysbr- Hardwood floors on main/upstairs levels; tile and carpet on the lower levelbr- Easy access for guests with limited mobility: just five stairs to enter, and primary suite on main levelbrbrOne well-behaved dog (1+ year old) is welcome for a $75 pet fee per stay.brbrWhether you're here for culture, quiet, or quality time, this thoughtfully designed home is the perfect Berkshires basecamp year-round.

4

Bed

4

Bath

8

Sleeps

$411.97

/ Nightly

Private Vacation Home

Available in June! Mountain Views, Fire Pit, AC, High Speed Internet!

Great Barrington, Massachusetts, United States

Renovated cottage with vast mountain views. 3 bedrooms, 2 full baths, sleeps 6. Amenities: backyard patio with seating, cafe lights, fire pit (wood included), propane BBQ grill, main floor bedroom with king bed and en suite bathroom, High speed internet/WiFi, 3 Smart TVs, washer/dryer, pack-n-play, highchair, fenced dog run, large backyard with outdoor games: soccer nets, balls, corn hole, bocce ball and the Appalachian trail just steps away! Central location! Pets considered with fee.brbrFirst Floor Features:brRenovated eat-in kitchen (seats up to 6) with pantry storage for your food, solid pots and pans, utensils, dishware, platters, etc. Perfect for longer stays!brKitchen appliances include: Dishwasher, Gas range/oven, microwave, toaster oven, toaster, blender.brCoffee station (Keurig, standard drip + French press) with kitchen lounge seating with mountain views: Plus 4 bar stools!brLiving room with sofa and club chair seating, reading nook, gorgeous nature views, and a 65 Smart TV.brMain floor Primary with king bed, ensuite bath with walk-in shower, TV, dresser, closet and Smart TVbrSecond bathroom with tub/shower combination and storagebrAttached 1 car garage with direct entry into the mud roombrFront entry mudroom, well organized for all your Berkshire gear, year round.brAttached garage with direct entry, automatic door clicker, room for 1 car, and ski storage. brbrSecond Floor:brGuest Room #2 with a full bed, dresser and closet.brGuest Room #3 with 2 twins, dresser and closet, and Smart TV + a few toys for the kiddos.brbrLower level:brThe washer and dryer is located in the laundry room in the basement.brbrOutdoor Features:brVast mountain viewsbrPatio with dining set, 4 wood Adirondack chairs a sectional sofa. 2 chaise loungers are avaialble for sunbathing or star gazing at night! brFire pit. (wood included)brBig backyard, flat, and perfect for outdoor games: 2 soccer nets, soccer balls, Cornhole, Bocce Ball included!brPropane BBQ grill and sun umbrellabrCafé lights set the mood! brFenced dog run - dogs must not be left and shall be monitored.brbrHiking: access to the Appalachian trail, is just steps away from Dixon CottagebrbrAdditional Features:brHigh Speed Spectrum cable internet and Wifi provided.brThe home is thoroughly checked prior to your arrival for an easy check in.brAll linens are provided.brProfessionally managed property - So you know you're in good hands!brBaby gear: highchair, pack-n-play - guest bring their own sheets, please brTanglewood picnic accessories: rolling cooler, and foldable chairsbrbrLocation: br5 minutes to downtown Great Barringtonbrless than 5 mins. to The Barn for live musicbr5 minutes to downtown Sheffieldbr15 minutes to Ski Butternutbr10 minutes to Catamount Skibr25 minutes to TanglewoodbrbrPets: Well behaved, trained pets are welcome with a $150 pet fee, per pet.

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Sleeps

$258.07

/ Nightly

Private Vacation Home

Cozy Riverside Berkshires Retreat

Great Barrington, Massachusetts, United States

Stay in our charming historic New England home right on the Housatonic river. This private half of a duplex offers river views, a fenced-in yard for relaxing outdoors, a fully equipped kitchen and easy access to the Berkshires. Downtown Great Barrington is a quick five minute drive and Tanglewood is only fifteen! brThe real treat is Studley, the sweet and much‑loved resident cat and “host with the most,” who lives on the property and is always happy to greet guests.

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Bath

Sleeps

$405.84

/ Nightly

Private Vacation Home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

New 3 BR rustic-yet-elegantly modern 2300 sq ft country castle set on on 3.5 secluded acres in Manor Lane, a private compound off Hurlburt Road in Great Barrington, MA, this property offers the perfect balance of peaceful seclusion and year-round convenience. We call it the GreatBarringtonCastle House, but it's much more farmhouse/luxury villa. Take the time to read the full description below -- you won't be disappointed.brbrCentrally located in the heart of the Berkshires in Smithsonian Magazine's Best Small Town in America 2015, Great Barrington. An idyllic basecamp to take advantage of spectacular hiking, biking, skiing, and views, with one of the longest, richly colored fall foliage seasons in the country, from September deep into October. When the winter snows fall, take out your snowshoes and experience the drifting silence of the woods. In summer, enjoy long days in nature and leisurely evenings. Fabulous local shops and restaurants rival any in the big cities. Great, quiet escape from NY City or Boston (or anywhere else). A great gathering spot for a family or group of friends.brbrThis private country home is spacious, extraordinarily comfortable, bright, cheery, uplifting, modern but not art deco, and not cookie-cutter. You’ll find that our house, the property, and the location are even better than in the pictures. The location is literally the best in Great Barrington, and the house is one of the most beautiful and unique homes in town, of any size. That's because we built our house specifically so we would never have a disappointing vacation rental ever again -- and you won’t either!brbrThe house is located on a beautiful, quiet country road, and still close to town. You don't have to choose between rural country life privacy and convenience when staying at this home -- it offers the best of both! Just down the road from Simon’s Rock, and 2 miles to famous Guido's or the center of downtown Great Barrington. The Appalachian trail or a swim at Lake Mansfield with a beach and lifeguard are just 5 minutes away, and it's 15 miles to the music and cultural events of Tanglewood to the north. ....Also makes an ideal ski haus, given that it's 5 miles to Butternut and Catamount ski areas, with an easy in, easy out property that's plowed with every snowfall, a ski rack in the garage to hold your skis, a spacious mudroom with plenty of hooks for your ski gear, the great room with rustic gas heating fireplace that lights up with the flip of a switch as soon as you come home from the mountain, and the chef's kitchen for ravenous appetites. All in all, a perfect four-season getaway!brbrNo expense was spared in rebuilding this home. Charming, bright, spacious modern farmhouse interior, with beautiful large windows throughout. A real gourmet chef’s kitchen with cathedral ceiling, pro range, SubZero fridge, and farmhouse sink, that's fully stocked with everything you could need, including a cabinetfull of spices, papergoods, three coffeemakers, and all the dinnerware, flatware, cookware and kitchenware you’ll need to entertain. And the water in the house is quadruple filtered, so the water coming out of the kitchen faucet is the best you've ever tasted! Seat up to 10 around the large, expandable rustic dining table. Beautiful, comfortable cathedral-ceilinged living room with huge premium sectional sofa, enough seating for a crowd. On rainy days or cold winter getaways, cozy up in front of the rustic fireplace. The grand master bedroom on the main floor has 11’ ceilings and a beautiful, large master bathroom. Another guest bedroom is on the main floor, and a third bedroom is up in the high tower, a favorite of adults and especially kids. All three bedrooms have outstanding, comfortable mattresses. (Another reason we built this house was because we couldn’t find a rental with comfortable mattresses!) Each bedroom has a beautiful private bathroom, with fully tiled shower with heavy glass shower door and Hotel-quality bath and bed linens. There's a well-appointed den with comfortable sofa, large desk, and computer monitor and laser printer to hook up to your laptop. Three large flat-screen TV’s are tastefully installed in the living room, master bedroom, and den, with excellent cable TV, internet, and cellular service, and high speed triband wifi throughout the house, along with direct ethernet jack plug-in to the network if you need it.brbrGas heat throughout the house ensures that you’ll stay toasty warm during the colder months. During the summer months, the main and second floors remain cool with the stone and wood floors and central air. The bedroom in the high tower has its own split unit for heating and cooling. There’s a new full size LG Washtower washer & dryer in a nice laundry/utility room. Plenty of books to keep you occupied, and dozens of cookbooks with recipes to try. Out back, there's a large patio with comfortable table and chairs, and Weber gas grill for summer meals. As Manor Lane is a rural, forested area, we have the house professionally treated with pet- and child-safe products every month by Orkin for ants, bugs, mosquitos, bees, and other critters, so you'll be comfortable and bug free dining outside at night on the patio. There's a single car garage for your use, with direct entry via mudroom into the house. The house has a keypad front door lock and wifi Liftmaster garage door, so you won't need any keys!brbrOur house was especially designed for weekly, monthly and longer term rentals, but we do accommodate 3-day weekend booking requests. We offer a 5% discount for weekly stays or more, and a 10% discount for monthly stays. Note that for stays less than 31 days, VRBO collects Massachusetts excise tax of 5.7% and Great Barrington tax of another 6%, for a total tax of 11.7%. The bright side is, stay 31 days and there's no tax, you save 11.7%! brbrNo smoking, and please inquire about children AND PETS before booking a stay. Sorry, we allow only one pet, and we can't allow cats.

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Sleeps

$997.6

/ Nightly

Private Vacation Home

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington, Massachusetts, United States

Don't hesitate reach out about availability even if dates look unavailable. We are happy to review avails with you.brbrA working farm located on more than 1000 feet of the Green River. Over 160 acres of beautiful woods and agricultural fields. Large indoor gymnasium with full basketball court, also good for indoor skating and roller blading. Babbling stream with pond right out the side door. A summer time wonder—but close to the local mountains for ski season.brbrbrNo weddings, parties, or events.

Bed

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Sleeps

$1414.9

/ Nightly

Private Vacation Home

Country Castle-Total privacy-just a few minutes from center of Great Barrington

Great Barrington, Massachusetts, United States

brbrWelcome to the Country Castle! This expansive home, boasting 7000 square feet, sits on 20 private acres less than five minutes (~2-miles) from downtown Great Barrington. It is also ~10-12 minute drive (~6 miles) to either Butternut or Catamount for a day on the slopes. The home is extremely private yet convenient to all Berkshire amenities. You can also meander from the backyard directly onto multiple hiking and snowshoeing trails to enjoy for hours.brbrThe space:brSet back from the road on 20 acres, a half mile long driveway leads you to this fabulous property with plenty of parking for your whole group. The main living space is open concept and is bathed in sun light and includes a large wood burning fireplace, connecting the kitchen, living room and dining room, creating the perfect space for a memorable occasion. The back deck is equipped with a BBQ and ample seating.brbrPerfectly designed with multiple rooms to stretch out and share time with family and friends. Amenities include an entertainment room with 75” TV and theater seating, pool table, and 9 foot tabletop shuffleboard game. A complete chef’s kitchen for the culinary enthusiast, equipped with stainless steel Viking appliances and all cooking essentials. A small gym with peleton style bike and weights. The residence includes a fire pole, drawing room, and meditation space accessed by a ladder in the main living room. There is also a large elevated deck located off of the main living space as well as a lower deck with a small fire pit and even more seating. Multiple offices allow for remote work away from your group during your reservation.brbrSix bedrooms and three baths, with plenty of private spaces to rest after a long day of exploring. The primary bedroom includes a king sized bed and full bath. Bedroom 2 and 3 both have queen sized beds and are connected with a Jack and Jill bathroom. Additionally bedroom 2 has a trundle bed, providing two single mattresses. Bedroom 4 and 5 both have queen sized beds, and share a bathroom in the hall. Bedroom 6 is accessed by a circular staircase and has connected twin beds. perfect for the little ones.brbrGuest access:brGuests will have complete access to the home, except for the plunge pool and the garage.brbrOther things to note:brThis home has stairs throughout and might not be satisfactory for guests that are disabled.brbrWe allow 2 well behaved dogs, and charge a $100 fee for either 1 or 2 dogs. Please include your pet when making your reservation.brbrNo cats please.brbrWe offer monthly discounts. Please make a booking inquiry for monthly rates as they vary through the seasons.

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Sleeps

$878.16

/ Nightly

Private Vacation Home

Sunsets On Blue Hill, Newly Renovated Farmhouse

Great Barrington, Massachusetts, United States

Summary:brbrWelcome to Great Barrington! The heartbeat of the Berkshires!brbrbrbrThis newly remodeled home is conveniently located in a quiet neighborhood on 1 acre, 5 min drive to downtown Great Barrington, and 5 min drive to Butternut Ski. Convenient to all South County attractions, culinary experiences, cultural and artistic events!brbrbrbrThe Space:brbrOur wrap around porch with sunset views is the perfect place for your group to enjoy you’re morning coffee or evening cocktail. Open floor plan with a fully equipped chef’s kitchen. Stainless 6 burner Viking stove, Viking commercial grade hood, farmer’s sink, stone countertops, dishwasher, and ice maker complete the kitchen, making it a dream for culinary enthusiasts. brbrbrbrStylish mud room has radiant floor heating. Cubbies and hooks for all your coats and hiking boots, as well as a 3/4 bath for a quick shower after your hike, bike ride or rinse off your four legged friend.brbrbrbrLiving room/dining room space is ideal for a family gathering after an exciting day of exploring. Large dining room table as well as abundant seating, allows everyone to spread out and relax. Open, airy, and filled with natural light this space creates a perfect atmosphere for any occasion! Easy access to the wrap around porch, furnished with Adirondack rocking chairs, allows you multiple places to enjoy the view!brbrbrbrSmall bedroom/playroom is right off the kitchen, includes one twin bed in addition to books, games and children’s toys.brbrbrbrLeading up the homes original stairway, you will find three bedrooms, two baths and laundry.brbrbrbrThe primary bedroom features a king sized bed, flat screen smart tv, remote work station, private balcony and luxurious bathroom. The bathroom includes a walk-in shower, soaking tub, top quality linens, and radiant heated floors. Reflect on the balcony with a cup of tea while taking in the evening air, or cuddle up and watch a movie in privacy.brbrBedroom 2 includes a comfortable queen sized bed, and sunset view.brbrBedroom 3 includes a full, and queen size bed. Perfect spot to group all the kiddos in. brbrbrbrAn additional bathroom on second floor with walk in shower, radiant heated floors and stylish finishes. Washer/Dryer on second floor. Thoughtful toiletries for each guest in case anything was left at home.brbrbrbrOutside you will find a large fenced yard for children and pets to play. Wide gravel driveway, stone patio, fire pit with seating and BBQ, great for summer cook outs.brbrbrbrWe have enjoyed creating this space, and are excited to share it with you! We hope to make your reservation a special one for you and you’re whole family!brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrGuest Access:brbrGuests will have access to the entire home and property, except for the basement.brbrbrbrThe Neighborhood:brbr4 min drive to downtown Great Barrington, and a 5 min drive to butternut ski mountain, our home is convenient to town. Our home is in a pleasant neighborhood on the north side of town.brbrbrbrGetting Around:brbrWe have parking for up to 5 cars.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brbrbrbrDamage: Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart. Damage related to pets is not covered under this waiver. brbrbrbr-Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrbrbrInteraction with Guests:brbrWe live in the area and can offer assistance if necessary, but will respect your privacy and will not visit the property during your reservation.

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Bath

Sleeps

$506.43

/ Nightly

Private Vacation Home

Great Barrington Lakeside Getaway w/ Kayak & Grill

Great Barrington, Massachusetts, United States

Enjoy stunning water views and lakeside fun at this 4-bedroom + den, 4-bath vacation rental in the Berkshires. A mixture of older appliances and modern amenities, like 2 large decks and a kayak, makes this home a bright and comfortable nature retreat. Enjoy eclectic shops, galleries, and farm-to-table restaurants only a few miles away in the vibrant town of Great Barrington. Check out attractions like Tanglewood, Butternut Basin, Jacob's Pillow, museums, and bike trails on the Appalachian Trail.brbr-- THE PROPERTY --brbrPermit: C0462781130 | 6 Mi to Skiing | Fireplace | Hiking, Skating, Ice Fishing, & Swimming (On-Site) | Fast EV ChargerbrbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: Full Bed | Den: Full FutonbrbrOUTDOOR LIVING: Gas grill, kayak, wraparound deck, lake w/ spacious dock (walking distance), walking trails nearbybrINDOOR LIVING: Board games, en-suite bath, flat-screen TV, jetted tub, fireplacebrKITCHEN: Dishwasher, microwave, stove/oven, dishware & flatware, cooking basics, toaster ovenbrGENERAL: Linens, dryer, hair dryer, iron/board, complimentary toiletries, keyless entry, laundry detergent, towels, trash bags/paper towels, free WiFi, central heating, central air conditioning (older unit)brACCESSIBILITY: 2-story home, exterior staircase required, interior steps required to access bedroomsbrFAQ: Quiet hours (8:00 PM-8:00 AM), 152 steps required to reach lake (waiver may be required), gun club nearby (may occasionally hear gun shots)brPARKING: Driveway (4 vehicles)brbr-- THE LOCATION --brbrWINTER FUN: Butternut Ski Area and Tubing Center (6 miles), Catamount Mountain Resort (10 miles), Bousquet Mountain Ski Area (15 miles), Jiminy Peak Mountain Resort (29 miles)brSUMMER SUN: Housatonic Flats Reserve (5 miles), Fountain Pond State Park (5 miles), Monument Mountain (5 miles), East Mountain State Forest (7 miles), Edith Wharton Park (13 miles), Appalachian Trail (14 miles)brTHINGS TO DO: Berkshire South Regional Community Center (5 miles), Norman Rockwell Museum (5 miles), Berkshire Botanical Garden (6 miles), Lee Premium Outlets (14 miles), Canyon Ranch Lenox (14 miles)brAIRPORTS: Albany International Airport (51 miles), Bradley International Airport (76 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This charming property is on the lake and is the perfect place to relax. This is an older property with stunning lake viewsbr- NOTE: This 2-story home requires using an exterior staircase to enter; additional interior steps are required to access the bedroomsbr- NOTE: Please observe quiet hours from 8:00 PM to 8:00 AMbr- NOTE: There are 152 steps on a long wooden staircase required to reach the dock at the lake. These stairs are not shoveled or cleared of ice in the winter. A waiver may be required before using the stairsbr- NOTE: There is a gun club down the road and occasionally, usually on a Sunday, you may hear gunshotsbr- NOTE: This home offers old-fashioned appliances and quirks. While not a luxury property, it offers all the essentials for a pleasant stay!

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Sleeps

$730.34

/ Nightly

Private Vacation Home

Renovated Downtown Great Barrington House

Great Barrington, Massachusetts, United States

Summary:brbrNewly renovated three bedroom “on the hill” in Great Barrington awaits your next family stay. Short walk to downtown Great Barrington for dining, easy stroll to Lake Mansfield for swimming or fishing, and walking trails. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 3 minute walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more!brbrbrbrThe Space:brbrEnjoy all day sunlight in this Berkshire gem which is set 100 feet off the road in it's own private setting. Watch the sunrise over the mountain trees while you have your morning coffee and breakfast on the lounge deck off the kitchen. As the sun rotates around the house throughout the day so can you from the kitchen deck to the deck off the living room to enjoy outdoor dining, BBQ, and a gas firepit. In the evening you can choose to also enjoy the wood fire pit with views of town, the mountains, stars, and a rising moon.brbrbrbrChef’s kitchen complete with a seamless 10 foot quartz countertops that seats 5, gas stove with range hood and microwave. The quiet dishwasher makes cleaning up a breeze. It’s an eat-in kitchen with space for five at the counter and eight at the dining table with views of the mountains and great sun and moonlight.brbrbrbrJust beyond the kitchen is the living room with a decorative fireplace. Plenty of seating with designer leather sofas and accent chairs. Large smart tv so you can log into your streaming apps or there are plenty of cable channels through Sling. The house is stocked with games that the family will enjoy which you can play at the kitchen table, island, lounge seating area, or TV seating area. While someone is watching TV you can be in the lounge playing games but also enjoying the company of everyone else.brbrbrbrSpace for up to eight guests, here is the bed layout for easy planning:brbrBedroom 1: king size bed in the main bedroom with streaming capability tv. Tufted Needle memory foam mattressbrbrBedroom 2: two queen size beds - 12 inch memory foam mattressbrbrBedroom 3: one queen size bed - 12 inch memory foam mattressbrbrbrbrTwo fully renovated bathroom with shower/tub combo. Rain shower head and handheld for convenience for showering or bathing.brbrbrbrThe home is a peaceful retreat with mountain views out front and on the sides. Sit outside and enjoy the Berkshires with your outdoor dining area, cook up tasty meals using the bbq gas grill or kitchen, and enjoy the evening either by the wood fire pit or the gas fire pit. You will see wild life including deer, foxes, birds, hawks, and lots of nature sounds with great flowers. This quiet yet centrally located home is a peaceful escape while being close to the action. Lake Mansfield is a few minutes around the corner where you can find a beach and dedicated swimming area with a lifeguard on duty certain days and times. There are picnic tables and BBQs, fishing areas (catch and release), and a nice flat manicured walking trail through the woods.brbrbrbrOther amenities worth noting:brbr-Central heating to keep you warm this winter.brbr-All the bedrooms, living room and kitchen all have window-unit AC to keep you cool during summer months.brbr-Wide plank pine floors in the living spaces and rugs in the bedrooms.brbr-Easy one floor living, easy path to the front door then a single step to get into the house.brbr-Laundry room with washer and dryer.brbr-Fast wifi throughout the house.brbr-Parking for up to 6 cars,brbr-All mattresses are memory foam with cotton sheets and a comfy down alternative duvet and four pillows.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrGuest Access:brbrEverything you need for a great stay, toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!brbrbrbrThe Neighborhood:brbrWalking distance (~2 mins) to downtown and all the great restaurants/shops that Great Barrington has to offer.brbrbrbrWalk to hiking trails and the lake from the house or take a quick 5-10 minute drive to many more hiking trails in the mountains and lakes.brbrbrbr20 minutes to Tanglewoodbrbr15 minutes to Lenoxbrbr10 minutes to Stockbridgebrbr5 minute drive to Ski Butternutbrbr20 minutes to Catamount Skiingbrbr30 minutes to Jacob's pillowbrbr25 minutes to Bish Bash Fallsbrbr20 minutes to Becket hiking areabrbrMuch more - check out our guide for more suggestions and things to do!brbrbrbrGetting Around:brbrYou can arrive and park your car and then walk to everything you need from grocery stores, convenience stores, shopping, restaurants, coffee, bars, and much more! Or a short drive will get you to everything you need and more.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no pets, no smoking, no partying, and being respectful of the neighbors apply. Security cameras located in the driveway, and the front and rear entrances.brbrbrbrIf you are booking through VRBO: You agree that The Host will charge your card for the full payment of the stay 24 hours after booking. Any payments by VRBO (service fees) will be charged separately. brbrbrbrDamage: Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

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Sleeps

$1647.89

/ Nightly

Private Vacation Home

Rosecliff: Ultra-Lux Pool, Big Views, Green River, Sleeps 15

Great Barrington, Massachusetts, United States

Rosecliff Amenities: Main House, Heated Pool with Pool house, Sleeps 13 in beds or 15 max. high speed WIFI internet and good cell service, Smart TVs with Streaming TV channels, central AC throughout, several areas for outdoor seating, sun umbrellas, (2) propane grills, mountain views, all high end appliances, sun room, washer/dryer (3), several gas and wood burning fireplaces, attached garage, easy access to all Berkshires venues - close to both Butternut and Catamount, less than 5 mins to the center of Great Barrington. NO smoking, please.brbrWelcome to Rosecliff! We are so happy to present this exceptional Berkshire estate that includes the main house, heated pool, and pool house. The main house has 5 bedrooms with 5 ensuite bathrooms plus 2 half baths and sleeps up to 11 in beds or 13 max (with an additional sleep space sofa bed). The pool house sleeps 2 more guests with another full bathroom and is fully heated, and cooled, and can be made available year-round. The main house is 9,500 sq ft. This property is so lovely and has so much to offer. The house sits back far from the country road and is welcoming the minute you pull in. brbrThe main floor has a entry that leads into the bright open kitchen. The appliances are all stainless, with plenty of storage, gadgets and prep space that offer guests a premier cooking experience - whether they want to create their own meals or bring in a local chef. There is a large farmhouse style table for casual dining and another gracious dining room, with a cozy propane fireplace, for more formal gatherings. The kitchen has big meadow views and is sun-filled. There is a small sitting area between the kitchen and dining room that offers a cozy space, with a full wet bar consisting of a dishwasher, ice maker, sink and wine cooler. Continue past the dining room to the large living room with another fireplace and plenty of seating. There is a cozy media room with a large TV for streaming all your favorite channels. There is still more to enjoy on the main floor with a summer sun porch and another parlor for easy gatherings, with seating and beautiful views. Just outside, on the covered patio is a lovely set up with seating and a grill for taking in the late afternoon views and sunsets. brbrUpstairs you have all 5 bedrooms - each with ensuite bathrooms - plus an additional bonus Playroom that has a fold out sofa for another guest or 2. This area has its own entrance through the back staircase and has another large TV, an efficient kitchenette with microwave, fridge, and coffee maker, etc. It also has its own full bathroom, with a shower. This is a terrific kid's space for TV viewing, gaming and is perfect for a nanny or babysitter. brbrThe 5-bedroom suites are fabulous - each with its own style and attention to detail. The primary is grand with beautiful views, a king bed, sitting area with gas fireplace and its own TV, a large dressing area and the best primary bathroom around - with a huge walk-in shower, soaking tub, 2 sinks and another sitting area. Guest room #2 has another king bed and its own brick gas fireplace. The ensuite bathroom has a luxurious clawfoot soaking tub and a walk-in shower. Guest room #3 has 2 Twin beds, built-in closets and drawers, and an ensuite full bathroom with a tub/shower combination. Guest room #4 overlooks the pool and has a Queen bed and a Twin daybed so 3 can easily sleep here. This ensuite bathroom is a “Jack n Jill' style and shares with guest room #5. The bathroom has its own walk-in shower and another glorious soaking tub. This beautiful bathroom also has a small Juliet balcony. Guest room #5, also overlooks the pool, has a Queen bed and its own TV. The bonus playroom is located on the second floor, up the back staircase, and can also be accessed on a roof deck off the primary bedroom and guest room #2. It has another TV and is a great space for kids as well as a Queen sofa bed for added guests and has its own kitchenette. brbrThe Pool house, located less than a minute's walk from the main house (heated, also with AC) offers another option to guests with a king bed, sitting room with mountain and meadow views, has its own kitchenette, TV, and full bathroom with walk-in shower. There is another terrific full kitchen just adjacent to Pool House, known as the “Cook Shack”. This area has its own fridge/freezer, range, dishwasher, utensils, set ups, etc., and another bathroom so there is no need for swimmers to drip water into the main house or pool house. brbrOutside, there is so much to enjoy here on this 16+ acre spread. The heated pool has plenty of both lounge and table seating, umbrellas for shade, another grill, and striped pool towels are included. The pool has easy access to the pool house and cook shack. The lawn is vast and lush and offers plenty of run-around space. There is a marvelous outdoor seating area just outside the kitchen with a stone patio, grill, ultra-lux seating and a fire pit. This is a stunning way to end the day, overlooking mountain and meadow views. brbrLocation: Rosecliff is less than 5 minutes to the center of Great Barrington, less than 15 to Ski Butternut and less than 10 to Catamount. And, just about 30 minutes to Tanglewood. Rosecliff offers our guests everything possible in a luxury retreat with close access to all the Berkshire has to offer. brbrMain House Guest Room Bed and Bath Recap : sleeps 11 in beds or 13 maxbr(All on second floor):brPrimary Ensuite: King bed, soaking tub, and oversized walk-in shower.brBedroom #2, is ensuite: King bed, shower and soaking tub.brBedroom #3, is ensuite: 2 twin beds, with tub/shower combination.brBedroom #4, Queen bed and twin daybed.brBedroom #5 has a Queen bed.brGuest bath is shared, Jack 'n Jill style between Guest rooms #4 and #5brbrBonus Playroom has a kitchenette, full bathroom (tub/shower) and a Queen foldout bed.brbrPool House: Sleeps 2 more guests in a king bed, kitchenette, and full bathroom with shower.brbrTotal sleep capacity in beds is 15.

Bed

Bath

Sleeps

$364.7

/ Nightly

Private Vacation Home

Home in Great Barrington

Great Barrington, Massachusetts, United States

{STAND ALONE UNIT}. Central and Private!! brJust steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy sunset views with friends and family before you walk into town for a night out! brThis brand new home features all new appliances and furniture. brEnjoy the comfort, charm, and privacy of home while you rest easy at the Maple. P.S. 413/717/7240 feel free to call at any reasonable time for questions. Always call at any time with an emergency. I’m here to help. Thanks

Bed

Bath

Sleeps

$529.33

/ Nightly

Private Vacation Home

5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!

Great Barrington, Massachusetts, United States

NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street name.)brbrBOOKING FOR THE REST OF 2025 AND THROUGH 2026! brbrAfter a fully booked summers through 2024 and mostly booked for summer 2025 (a few spots remain open!), we are booking for the remainder 2025 and all of 2026. We are excited to see returning guests as well as new ones. brbrOur five bedroom, three bath, two fireplaces, and two large 'family' rooms are ready for you and your guests. Almost three acres of property give you privacy, but you are less than 2 miles from Great Barrington, 5 minutes from Ski Butternut, and inches away from a spectacular views of New England 'country' life. Local restaurants for all tastes abound, our kitchen has all the implements you need for staying at 'home' for a meal. brbrAnd the house you'll be renting - about that:brbr A week, a month, a weekend, or a few days in the beautiful Berkshires - - what could be better Located 130 miles from NYC and from Boston, this “rustic” yet modern beloved family vacation home in the heart of the Berkshires is available year-round. With five bedrooms and three full bathrooms this house easily sleeps 10 in bedrooms, with another double futon in the family room, and plenty of room for extra visitors as you wish. Seat 10-12 around the dining table, in the screened-in porch, or on the spacious deck overlooking the 20 x 40 in-ground pool (closed mid-September until Memorial Day weekend). Ready for campfire time We have a fire pit all ready for you. Renovated kitchen with new refrigerator and dishwasher is fully equipped for indoor cooking as well as the outdoor gas grill. On those cool or cold nights, cuddle up in front of one of two wood-burning stoves (in the family room or in the living room.) Living room also has a two-story cathedral ceiling with floor to ceiling windows overlooking the pool and yard. Privacy abounds on our 3 acre lot, but access to Great Barrington is easy - 1.6 miles away! When the pool is closed (it is unheated - so you want it closed off-season!), you still have two family rooms, two wood-burning stoves, a Jacuzzi tub and more to relax; you can shoot pool, play games, stream movies, watch tv, and spend time catching up on your reading and fun. Plenty of books, games and puzzles available for your use. Have little ones We can supply portable cribs, high chairs, bedguards and even potty-trainers! We even have a toddler 'playground' out back (turns out our grown kids don't need it any more. Been there, done that!)brbrFive bedrooms include two 1st floor bedrooms (one with a double bed, one with two twin beds that can be made up as a king-size bed), two 2nd floor bedrooms (one with a double bed and one with a brand-new queen! and a primary suite above the family room at the opposite end of the house. Primary suite has king-size bed, two walk-in closets, and a bathroom with double-nozzle shower and separate Jacuzzi tub. There are two additional shared full bathrooms in the main part of the house, one downstairs and one upstairs. Hair dryers provided. You'll stay warm (and cool, as appropriate) with our ductless heat pump heat and air conditioning systems throughout the house - every room has individual thermostat controls if you need heat in addition to the heat pump systems and wood stoves (we are fully stocked with firewood!)brbrFirst-floor laundry room with full-size washer & dryer and closet rod to hang freshly laundered clothes and a tiled floor to dry out your skis and boots. Ironing board and iron provided. Linens provided. Beach towels & pool play toys provided. brbrElectronics: Wi-Fi, Cable TV (Spectrum), 5 Televisions ( all Flat Screen), and strong mobile phone service. brbrReady to leave the house It’s hard… but the house is less than 2 miles from Great Barrington with its restaurants and shops, 3 miles from Ski Butternut, 6 miles from Norman Rockwell Museum, 6 miles from Stockbridge, 10 miles from Tanglewood Music Festival (summer season), Jacobs Pillow Dance Festival (summer season), 11 miles from Lee Premium Outlet Mall, and more. Lakes, ponds, hikes, and walks. Whether you prefer hiking a portion of the Appalachian Trail or nearby Bish Bash Falls (Massachusetts highest waterfalls), or visiting Ashintully Gardens in Tyringham to fly fishing in local streams - so many wonderful outdoor activities. The Audubon Society's Pleasant Valley Wildlife Sanctuary's 7 miles of trails through their 1,132 acres in nearby Lenox, and you can go taste fresh maple syrup at Ioka Valley Farm's cafe. More of an indoor fan - how about a spa visit or yoga class (or two) at the Kripalu Center or Canyon Ranch in Lenox Looking for the 'arts Edith Wharton's beautiful home in Lenox, The Mount, is only a few miles away, another Victorian home Ventfort Hall, was built by the Morgan family (of JP Morgan fame) and is now open for to visitors. Of course the restaurants are open, the Triplex Cinema in Great Barrington is showing first run and classic films, the art galleries and antique shops await you. So much to do and see.brbrPortable lawn chairs provided to take on family outings (e.g. to Tanglewood Music Festival). brbrOutdoor shed with room to park bicycles or sleds you might bring.brbrThe beauty of the Berkshires is year-round – and this house can be your home-base for all of it. brbrPlease note: If you are looking for a Hamptons-like mansion, we hope you find your dream vacation home. This isn’t the one. If you want a place that you can play, eat, sleep, relax, spread out and enjoy – we hope you give our home a try!brbrQuestions Let us know! We will be providing an extensive guide to the house and area for your stay - but in the meantime, ask away. If we don't know the answer, we'll find out for you!

Bed

Bath

Sleeps

$1004.51

/ Nightly

Private Vacation Home

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington, Massachusetts, United States

Luxury 4-Bedroom Retreat | Hot Tub • Pool Table • Gym • Spacious deck & lawn.brWelcome to your private getaway — a beautifully designed 4-bedroom, 2-bath luxury home that blends comfort, style, and upscale amenities for a truly unforgettable stay.brUnwind in the outdoor hot tub under the stars, challenge friends and family to a game on the full-size pool table, or keep up your routine in the fully equipped fitness room. Whether you're gathering in the open-concept living area or relaxing outside on the expansive deck, there’s space for everyone to feel at home.br 4 Comfortable Bedrooms – Thoughtfully furnished with quality linens and stylish decorbr 2 Modern Bathrooms – Clean, elegant, and fully stocked with essentialsbr Large Private Lawn – Perfect for outdoor games, lounging, or enjoying your morning coffeebr Hot Tub – Your own private spa experiencebr Pool Table – Great for friendly competition or casual evenings inbr ️ Fitness Room – Includes cardio and strength equipment for daily workoutsbr ️ Fully Stocked Kitchen – Ready for cooking, dining, or entertainingbr Fast Wi-Fi & Smart TVs – Stay connected and entertainedbr Free Parking On-SitebrLocated in a peaceful neighborhood, you're just a short drive from [local attractions, restaurants, or nature spots], making this the perfect home base for families, groups, or professionals seeking a stylish escape.brWhether you're here to relax, explore, or celebrate, this home offers the comfort of a boutique hotel with the privacy and warmth of a personal residence.

4

Bed

2

Bath

8

Sleeps

$1135.62

/ Nightly

Private Vacation Home

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington, Massachusetts, United States

Well appointed Vacation Cottage, newly renovated by the Owners; An Architect and an Interior Designer as a Modern Farmhouse. br5 bedrooms, 4 bathrooms, 2 large living rooms, an entertaining playroom and a well-equipped Kitchen, Front and Rear covered porches w/ a Hot Tub overlooking the open forest view.brThe large open lawn hosts volleyball net, soccer goals, picnic tables with lighting for outdoor dining, Solo fire pit sitting area, BBQ grill and yoga matts for your early am flow.brThe Hot Tub for 5 is conveniently located under the covered rear porch overlooking the forest. 5 min drive from Lake Mansfield and the town of Great Barrington and other beautiful surrounding hiking trails.brComplete privacy yet only about 10 min drive from 2 Ski resorts, Butternut & Catamount. 5 min drive from Lake Mansfield and the town of Great Barrington and other beautiful surrounding towns with many options for Restaurants, Shopping, Balling Ally’s, Music & Theatre events and festivals & hiking trails, one would never get bored. brbrClimbing only 3 steps to the front deck, entering the house into a double ht. foyer that leads to an open floor plan brbrThe house is fully air-conditioned/heated with ample storage and closets for shoes, ski gear and coats. Walking into an open floor plan; Kitchen, Dining & couched Fireplace sitting area & Living Rooms.brbrThe kitchen is fully equipped and has an eat-in island (sits 5). The dining table is large enough to for great family and friends gatherings.brbrThe house has 2 separate large Living Rooms, each equipped with 75” HD smart TV and large sectional sofas.brbrThe playroom includes a full size double Pop-A-Shot (double hoop basketball game), Air Hockey table, a Foosball table, XL Janga, Remi cube, Bingo and other board games.brbrThe Laundry room equipped with 2 Washer machines and 2 Dryers.brbrThe 2nd floor includes a Yoga space / Sitting area overlooking the forest, 2nd Master bedroom, oversized King room with office space and anther bathroom with tub. brbrBedrooms:br#1 - Master Bedroom #1 - On First Floor - Queen size bed with private oversize bathroom & jungle shower with 2 windows overlooking the woods while you shower.brThe Bedroom includes a comfortable armchair & side table, light night, closet and dresser.brbr#2 - Master Bedroom #2 - On 2nd Floor - Queen size bed with private bathroom & jungle shower. brThe Bedroom includes a comfortable armchair & side table, 2 light night, closet and dresser.brbr#3 - King Bedroom - On 2nd Floor - Extra Large bedroom with a King size bed and a pull out twin bed and a twin open sofa The room has an eclectic collection of furniture to provide comfort and function with a reading nook. The Bedroom includes a comfortable armchair & side table, light night, closet and dresser.brThe full bathroom with a tub is across from it. brbr#4 - Queen Bedroom - Queen size bed with a built-in loft over it with a twin mattress. The Bedroom includes a side table, light night, closet andbrDresser.brbr#5 - Bunk Bedroom - Sleeps 4 on twin size mattresses on 2 bunk beds. The Bedroom light night for each bed personal cabbie unit for each of the 4 guest.brbrThe 4th full bathroom is located on the first floor.brbrEach Queen bed has 4 pillows (2 down pillows and 2 alternatives and a down comforter).brbr- An Office / Open Gallery Space is located on the upper floor with a sofa and a trundle bed under it, providing additional two twin size sleeping beds arrangement.brEach guest gets 2 large towels. brImportant highlight features - Covid prevention Committed, Completely fenced backyard, private parking spaces, Strong WiFi, the house is Fully Air-Conditioned.brbrNight light for each bed and Designated storage space for each of the guestsbrEuropean comfort - all bed linens are are 100% Cotton/400-600 thread.brDown pillows & white goose Down comforters.brbrThe Cottage has an Alarm system and security cameras that are directly connected 24/7 Fire & Police departments. Outdoor Solar lights around the back yards. And a smokeless fire pit (Solo) & Hot Tub for 5.

5

Bed

4

Bath

16

Sleeps

$879.7

/ Nightly

Private Vacation Home

5 Stars w/ Hot Tub, Sunny Patio, Game Room, Views!

Great Barrington, Massachusetts, United States

White Birch amenities include 4 bedrooms, 3 baths, Sleep 12+ a main floor master suite with a large walk in shower, hot tub, high speed internet, 5 Smart TVs with access to streaming channels like Netflix, etc and a Sonos sound system, Ping Pong, Foosball table, Nintendo Wii, mini-split wall unit air conditioners, brand new appliances including a gas range, washer/dryer, EV car charger, standard drip coffeemaker, and a dishwasher. Outside you will find beautiful mountain views, a fire-pit, outdoor seating, propane grill and the Appalachian Trail that is only a short walk down the road. The home is located only 10 minutes to Great Barrington, 15 minutes to Stockbridge, and 25 minutes to Tanglewood. Pets are considered with a $150 pet feebrbrMain Floor: This perfectly renovated, open concept home is full of natural light, mountain views, and stylish touches throughout. The home is situated beautifully between 2 mountains and is only a short walk from the Appalachian Trail, which is perfect for anyone who loves to hike! The bright and open living room consists of comfortable seating and a large smart TV with Roku streaming channels like Netflix, Hulu, etc (no cable channels). There are plenty of fun board games and puzzles to keep friends and family entertained. Just off of the living room is the well appointed kitchen that has brand new appliances, tons of storage, a large kitchen island with seating and lots of prep space for the home chef. Next to the kitchen is the dining room with a table that comfortably seats 10+. The large main floor master suite boasts a king size bed, smart TV with streaming channels, a queen size sleeper sofa, and an en suite bathroom with a large glass and tile walk-in shower. Just off of the living room is another bedroom with a queen size bed. There is an additional full bathroom with a tub/shower combination. Lastly, the the washer and dryer is also located on the main floor for the guest's convenience.brbrUpstairs, there are 2 more bedrooms and a full bathroom with a tub/shower combination. One bedroom has 2 queen size beds and a Roku TV, while the other has 2 bunk beds (double on the bottom and single on top) and a twin size bed. This bedroom can sleep 4 adults comfortably or 7 kids. At the top of the stairs, on the landing, there is a comfortable reading chair to soak up the sun and catch up on your latest book. brbrLower level Playroom: Guests can enjoy the newly finished basement with 2 TVs, foosball table, and ping pong! There is a Nintendo Wii with 20+ games and 6 controllers. It is the perfect hang out space for kids and parents alike looking for a fun place to unwind after a busy day sight-seeing or skiing. brbrOutside: Is a fabulous outdoor patio with lots of seating, a large fire pit, a hot tub that seats 4 to 6 people, and a propane BBQ grill. There are beautiful Mountain Views and the Appalachian Trail is only a short walk away, so you can literally walk outside your door and go for a hike. brbrLocation: This terrific location is less than 10 minutes to Great Barrington, 15 minutes to Stockbridge, and just 25 minutes to Tanglewood!

4

Bed

3

Bath

14

Sleeps

Select Dates for Price

Private Vacation Home

Newly Built 4 Bedroom Lake House with Kayaks & Paddle Boards!

Great Barrington, Massachusetts, United States

span style=font-family:Verdana,Geneva,sans-serif;Long Pond Views: New Built Contemporary with 4 bedroom, 4 full baths, sleeps 8 in beds. Amenities include access to the lake, 2 kayaks, 2 paddle boards, a main floor bedroom (with the master bedroom upstairs), a fire pit (wood included) Adirondack chairs, hammock, sun deck, Weber grill, 4 smart TVs, high speed internet and wifi, bright kitchen, washer/dryer, central AC, ping pong table, lovely water views. All linens included. Pets are considered with a $150 pet fee, per pet. No Smoking, brThis brand new construction home is light and bright with plenty of thoughtfully designed space to be able to spread out and enjoy Berkshire living, at its finest! The large and open kitchen has everything the home cook needs along with plenty of counter space and storage. A brand new state-of-the-art electric oven range was installed October, 2023 for an even better cooking experience! There is a huge island, a standard coffee maker and a Keurig coffee maker, toaster, vitamix blender, a microwave...and more. We have it nicely equipped for a guest to easily prepare and serve Thanksgiving dinner. The dining room table comfortably seats 8 guests along with 2 extra stools at the counter. The media room is just off the dining area and it has cozy seating, a Smart tv, and an area with yoga mats, a big ball and rollers for stretching and yoga. Boasting 4 bedrooms and 4 full baths, there is one main floor bedroom, with a queen bed, and three (3) other bedrooms upstairs (king, queen, and full). The main floor bedroom has a queen size bed along with a chest of drawers, closet, desk, Smart tv, and the shared bathroom is just across the hall with a walk-in shower and laundry room! There is also an office on the main floor with a desk, white board, monitor and printer - all for guests use. Please use a little and leave a little printer ink brThere are 3 more guest rooms upstairs, all good-sized, and each has its own full bathroom. The primary Guest room, with King bed, has a walk-in cedar closet and a lovely ensuite bath with large soaking tub and a walk-in shower. The third Guest room has a Queen bed, with its own ensuite bath with a walk-in shower. The 4th guest room has a Full bed and its own full bath (tub/shower combo) just across the hall.brJust off the dining area, sliding doors open onto the large patio and yard with views of the lake. There are plenty of comfy seating along with Adirondack chairs to relax in, a hammock, propane BBQ grill and a solo fire-pit, wood included. Take a short walk down to the water where you can swim, kayak, paddle board, or simply sit and enjoy nature. Round Pond is located right next to Long Pond and the 2 are often confused. This home has access to Round Pond, which is the larger of the 2, at 54 acres. (Speed boats are not permitted only trolling/electric motors.)brThe location of this home can't be beat - It's under 10 minutes to the center of Great Barrington, 15 minutes to Butternut, and 20 minutes to Tanglewood!

4

Bed

4

Bath

8

Sleeps

$640.09

/ Nightly

Private Vacation Home

Chic, Mid Century Modern 3 bedroom Home, Close to Downtown GB!

Great Barrington, Massachusetts, United States

Amenities Include: 3 bedrooms and 3 full bathrooms (sleeps 8 in beds), bonus finished basement game room, high speed internet/WiFi, AC throughout, 2 Smart TVs with streaming channels like Netflix & Hulu, Billiards Table/Air Hockey Table, All new stainless steel appliances, washer/dryer, 2 car garage with direct entry into the kitchen, fully fenced back yard, outdoor seating with propane BBQ grill, outdoor umbrella, seasonal fire pit, loads of fun toys and all the linens are included, too.brbrHill House Modern: a lovely mid-century modern boasting one-level living, with easy access to Lake Mansfield Park and the center of downtown Great Barrington. The house is light-filled, spotlessly clean, with thoughtful touches throughout. The front room has a cozy elegant seating area with fun battery operated candles in the fireplace for great ambience. There are books and games available and a large coffee table perfect for a puzzle or a board game. This is a great room to enjoy appetizers before dinner or to cozy up in with a book. The recently updated kitchen has all new stainless steel appliances which include: a refrigerator/freezer, electric range, dishwasher, microwave, toaster, and standard drip coffee maker. With plenty of counter space and kitchen, preparing your meals is a breeze. The kitchen is eat in with table seating for 6 along with additional counter seating for 3. The large media room is just off the kitchen and offers guests comfortable seating with it's oversized leather sofa & chairs, alongside a 65 Smart TV with access to all of your favorite streaming channels. brbrBedrooms: Head down the hall from the front room to the three (3) bedrooms and two (2) full baths. The primary bedroom has a king bed and ensuite full bathroom with walk-in shower. Guest room #2 has a queen bed and guest room #3 has two (2) full size beds. These 2 bedrooms share another bathroom #2, with a tub/shower combo.brbrLower Level: The fully finished playroom has a lot to offer: with billiards table that can convert into an air hockey table, another smart TV, sitting area, indoor basketball shoot-out game, doll house, toys, games, and more. This area is multi-purpose and also includes a craft table and other fun things to do for kids of all ages. The laundry room is also located on this lower level.brbrOutside: The backyard, fully fenced, is easily accessed through the media room. There is a crushed stone patio has a dining table and chairs, outdoor umbrella, chaise lounge and propane BBQ grill. There is also a fire pit for guests to enjoy.brThe garage is attached and provides an easy access into the kitchen and ample storage place for snow gearbrbrLocation: The house is an easy walking distance into town as well as to Lake Mansfield, with a sandy beach, swimming (lifeguard on duty in summer), picnic tables, swings, play structures, standing charcoal grills and hiking trail - all less than a 1/2 mile from the house. The center of Great Barrington is also less than a mile away and offers shops, restaurants, bars, galleries, bakeries, coffee, movies and more to explore. Both Ski Butternut and Catamount Ski are just 10 minutes away and Tanglewood is only 25 minutes. You will not want to miss this sweetly re-done and perfectly located rental opportunity, granting you access to all the Berkshires has to offer.brbrNo smokingbrPets are welcome guests, along with a pet fee. brPlease see House Rules for more details

3

Bed

3

Bath

8

Sleeps

$661.97

/ Nightly

Private Vacation Home

Fall Weekends: Hot Tub, Green River Hike, Sleeps 8+

Great Barrington, Massachusetts, United States

Highland Amenities: 4 Bedrooms, 2.5 baths, Sleeps 10. Pet friendly with a fully fenced yard (pet fees apply), hot tub (year round) propane grill, outdoor seating w/ sun umbrella on patio + chaises for sun deck, lovely gardens, high speed internet, mini split AC, ice maker, wood stove (wood included), Smart TV, washer/dryer, games, all linens included, attached garage. Gate access to McAllister Park for hiking and swimming and close to Lake Mansfield, Butternut, GB Busking in Summer! No Smoking.

4

Bed

2

Bath

10

Sleeps

$680.25

/ Nightly

Private Vacation Home

Fireplace, Privacy, Screen Porch, 1 Level Living!

Great Barrington, Massachusetts, United States

The Garden House, Quiet Elegance with One-Level Living, in a Park-Like Setting. Sleeps 10brAmenities: 4 bedrooms, 4 full baths + 1/2 bath, Large screened in porch, outdoor seating with grill, large lush lawn, 3 Smart TVs, chef's kitchen will high-end stainless appliances, Spectrum Wifi, Air Hockey, Playroom, AC, Garage with access for 1 car, wood-burning fireplace, 2 washer/dryer sets. No Pets (no exceptions) No Smoking.brbrThe Garden House is your perfect one-level property for guests of all ages. The living room is inviting with 2 velvet sofas, a wood-burning fireplace, a baby grand piano (available, but not a toy) and game table. Tuck into the reading nook with many engaging books, suitable for both adults and children.brbrThe Kitchen: Skylights, gas fireplace, dining area+extra seating. Kitchen has direct access to the screened porch!br- 6 burner gas range, dishwasher, and custom freezer/fridge with ice makerbr- Small appliances include: standard coffee maker, electric water kettle, air fryer, blender.br- 2 islands provide ample counter space and oodles of storagebr- Adjacent screened-in porch with many seating options and outdoor lighting.brbrBedrooms and Layout: 4 bedrooms with 4 full bathrooms are all on one level. Sleeps br- Primary has a king bed, TV, ensuite full bathroom with X-large walk-in shower.br- Guest #2 has a queen bed, ensuite with a showerbr- Guest #3 has two twin beds and its own bathroom, with a tiled tub/shower.brOn a separate wing is The Apartment with Guest #4 bedroombr- Easily accessible from the main house, just down a short hall from the living room but also has its own private entrance.brThe apartment has a living room (with queen size pull-out sofa), Smart TV and a full kitchen snack space with drinks fridge and microwave. The bedroom with a Queen bed has its own bathroom with walk-in shower and stacked laundry.brbrOther features: lower level playroom with Air Hockey, Second laundry room in the basement, a 1/2 bath near the kitchen. Please see the floor plan for better understanding!brbrOutside: 3 acres of park-like lawn lawn, privacy. There is a small stone terrace with seating and lovely mature gardens.brGarage available for 1 car.brbrLocation: Perfect and central - close to all major Berkshire venues! Easy walk to The Barn for food and live music! Less than 10 minutes to the center of Great Barrington and only 30 minutes to Tanglewood. Ski Butternut and Catamount ski are both 10 minutes drive.brNo pets, no smoking.

4

Bed

4

Bath

10

Sleeps

$491.67

/ Nightly

Private Vacation Home

Pristine 3 Bedroom, Walk-to Gt Barrington Center!

Great Barrington, Massachusetts, United States

Amenities: 3 bedrooms, 1.5 baths, (sleeps 6 in beds or 8 Max.) WIFI, AC, SmartTVs with Spectrum cable, local phone, good cell service available, side deck with outdoor seating and grill, washer/dryer, walk-to Lake Mansfield and easy walk to the center of Great Barrington! NO SmokingbrbrCastle Townhouse is a delightful new listing, completely renovated, and in a wonderful central location - just steps to the center of Great Barrington and a few minutes walk to lovely Lake Mansfield! The portico welcomes you into the front foyer from the wrap-around front/side porch with outdoor seating. Just inside, there is a large main closet perfect for all of your Berkshire gear. The main floor is tidy with a sumptuous living room, complete with a new flat screen SmartTV, and very cozy seating. The kitchen is perfection with all new stainless appliances, a small wall-mounted TV, counter seating for 2, a huge island for prepping and a country style table that seats 6+. There is a darling small deck area off the kitchen door, which houses a gas grill during the warmer months.brUpstairs, you will find all 3 bedrooms: the master bedroom with queen bed, and two guest bedrooms -- one with a queen bed, the other with double (extra wide!) bunk beds. This third bedroom could sleep 2 adults, 2 kids (or even 4 smaller kids)... or a grandparent who wants to bunk in with small ones - there are many possibilities! These three bedrooms share a very large tiled full bathroom with a tub/shower combination, along with a large stacked washer and dryer. There is a 1/2 bath on the ground floor as well.brOutside, you have the wrap-around porch with seating, and the kitchen deck with a grill. There is room for two cars with off-street parking in the summer, and room for one car during the winter holiday periods. The Mahaiwe Performing Arts Center, Castle Street Cafe, and all of downtown Great Barrington is just a few minutes' walk from your door. This is truly a marvelous location!

3

Bed

1

Bath

8

Sleeps

Vacation Home Rentals By Owner In Great Barrington, MA

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$661.97

$680.25

$491.67

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