Vacation Rentals By Owner In Great Barrington, MA

Discover this enchanting folk Victorian farmhouse, a harmonious blend of vintage charm and modern convenience, just minutes from Great Barrington and Catamount or Butternut ski resorts. brThis house is perfect for family getaways. The gourmet kitchen boasts a *gorgeous* 4-oven AGA, the king of British country stoves, and there are two primary suites, plus 4 twin beds, enough to fit the whole family - or two! brSoon to come this summer! Fenced-in yard for dogs and an above ground swimming pool!

Farmhouse w AGA, 2 suites - close to GB & skiing

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$612

A lovely property with gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood & Jacob's Pillow. 6 rooms, 3 bedrooms (4 beds), 2.5 baths, sleeps 8. Rent entire two floors. Main floor has an open floor plan, making each room flow into another, including a spacious living room with a large smart TV, a fireplace pellet stove, an upscale & fully equipped kitchen, half bathroom, a dining area which opens to a deck with breathtaking view and a screened porch. The main floor also houses a master bedroom with a king size bed, an attached master bathroom (with deep bath-tub & a separate shower) and an office in a separate room. The upper floor has a bathroom with tub & shower and two bedrooms: one with king size bed, and the second bedroom has two queen beds (sleeps 4). The house has two residential units with separate access. The owners sometimes stay at the unit in the basement where the laundry room exist (you will have access to the laundry/dryer whenever you need). There is a sound barrier between the units to ensure privacy. The backyard has a large blue-stone paved patio, where you can recline, enjoy the view, barbecue, or sit by the fire pit to roast marshmallows. The house sits on 0.8 acres land is surrounded by trees to provide privacy. Enjoy the use of: 4 kayaks & 1 Canoe (you can roll it on an attached cart) to Lake Mansfield boat dock which is 300 feet away. This property is perfect for families, vacationing couples, or group of friends. House has central heating, AC units, smart TVs (in living room and all bedrooms) and high-speed internet access.

Gem of the Berkshires. Mountain View. Short walk to lake & downtown.

Great Barrington, Massachusetts, United States

Bed

Bath

8

Sleeps

Select Dates for Price

Situated just minutes from the town of Great Barrington, skiing at Butternut & beautiful hiking trails, you will find this modern, light-filled home.brbrSurrounded by lush gardens and filled with original artworks and luxurious touches, the home was designed by its massage therapist/ yoga teacher owner to be a peaceful space to rejuvenate & connect with friends & family both indoors and out.brbrHost is available to arrange personalized & group retreats if desired. Please inquire in advance.brThe spacebrNote: Please read the complete house description including house rules to make sure that the space works for you.brbrThe house is a 5 minute drive to the center of town, yet feels like an oasis. It is close to many hikes, and yet there is a coffee shop and many restaurants in walking distance.brbrBoth bathrooms are newly renovated to feel spa-like. Both have glass wall tile, multiple shower heads and are equipped with natural essential oils-infused soaps and shampoos. The downstairs bathroom has heated floors.brbrThe spacious kitchen (also with heated floors) has all the tools needed for cooking, and there is also a gas grill outside on the patio (as well as an outdoor dining area).brbrThe 3 main bedrooms have high quality queen -sized mattresses (Tempurpedic upstairs and beautyrest pillow-top and brooklyn bedding downstairs).brbrThe yoga room has an additional queen sized mattress which can be set up upon request as well as several yoga mats and props (blankets, straps, blocks and bolsters).brbrThe living room comes with games and Bluetooth-enabled sound system, but no television. There is a projector and movie screen in the theater room in the basement for movie nights (that can be hooked up to your computer through hdmi).brbrOutside in the garden, you will find plenty of places to lounge or read a book including comfy outdoor furniture and a hammock. There are flowers that can be cut and brought inside for bouquets throughout spring and summer (lilacs, tulips, daffodils, hyacinth, irises, roses, peonies, lilies, hydrangeas, and more!).brGuest accessbrThere is space in the driveway for 3 midsized cars, possibly 4 if smaller vehicles. If you will be bringing more than 3 cars kindly let me know to.make sure you will fit in the driveway.brOther things to notebrAll reservations include a $200 -$300 (depending on length of stay) cleaning fee which covers an end of stay cleaning.brbrPETS:brWe allow dogs (sorry, no cats or other pets) with the following agreements:brbr1. Pet Fee: There is a $200 dog fee included in your reservation when you indicate your are bringing a pet. The $200 fee is PER dog up to 3 nights (2 dogs max). Longer stays will require an additional fee of $50/ night per dog.brbr2. Damage to the house and property is not covered by the pet fee. You are responsible for covering the cost of any damage.brbr3. You are expected to bring a dog bed that your dog is trained to use.brbr4. Dogs are not to be left alone for periods of more than 4 hrs. If you will be leaving the dog for longer, we can connect you with a dog walker with advanced notice.brbr5. You are expected to pick up after your dog/ dogs must be leashed. $200 fee for dog feces left in the yard.brbr6. Dogs' feet are wiped off with wipes provided before coming inside the house.brbr7. Sorry, no puppies or elderly dogs-- they are just too accident-prone.brbrbrbrFor stays 28-days or longer, please note:br1) Stays of 28+ days require an additional $200 utilities deposit, which will be refunded so long as energy (gas/ electric) consumption is under $300 for the month. If usage exceeds this, it will be deducted from the deposit.brbr2) Stays of 28+ days include an additional mid-stay cleaning which includes vacuuming, mopping, dusting & cleaning surfaces in bathrooms and kitchen. It does NOT include washing linens or dishes— guests are responsible for this.brbrIf you would like more frequent cleanings or a more extensive mid-stay clean, we can arrange this at your convenience for an extra fee.brbrAdditional guests beyond 4:brPlease note that while the house can sleep up to 8 people, the dining room table can accommodate 6-7 max, so larger parties are not going to be comfortable in the house for more than a night or two. For this reason, we have a max of 6 guests for stays longer than 3 nights.brbrbrThere is a fee of $30per person per night for guests beyond 2. Please enter the correct amount of guests when booking your stay for accurate fees to be reflected.brbrbrFIREPLACE:brYou are welcome to use the fireplace, however there will be an additional fee to cover the firewood, a starter batch of fire-starters, and additional cleaning required. You must inform us if you intend to use the fireplace ahead of time so we can prepare it for you.br$35/ weekendbr$50/ weekbr$100/ month

Remodeled ski and summer retreat close to town

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$557

Summary:brCome enjoy country living in all seasons – on 4+ acres on a private lane yet only minutes to Downtown Great Barrington and Tanglewood. Your home for the week effortlessly blends inside and outside with lots of natural light, huge 1000+ square foot deck, large yard, multiple gardens, and outdoor hot tub. Bring your family and your one furry friend and enjoy this very special Berkshires home!brbrThe Space:brYour home away from home has everything you need to enjoy all that the Berkshires has to offer. You'll be situated on a short and relaxing drive to a huge variety of experiences: from downtown Great Barrington for shopping and dining; to an outdoor concert at Tanglewood or dance performance at Jacob's Pillow; to several world-class museums including the Norman Rockwell Museum, The Clark, and Mass MoCa; to several swimmable lakes and rivers; to numerous hikes, nature preserves and playgrounds.brbrThe large and inviting chef’s kitchen is the perfect place to gather after a day of exploring. The kitchen features a high-end Electrolux ICON dual oven and warming drawer, Liebherr fridge/freezer, wine fridge, and Thermador induction stovetop. It's also got all the necessary cooking/serving items including cookware, pots, pans, plates, bowls, glasses, stemware, mugs, and silverware.The counters are made of Vermont Danby marble and soapstone, and just off the kitchen is easy access to the large deck for indoor/outdoor dining and relaxing. brbrThe ice maker inside the freezer is turned off: There is a standalone unit that can make ice more quickly (every 10 minutes) on top of the beverage fridge.brbrThe dining table seats up to eight, and the countertop seats up to four: Plenty of open space in which to prepare and enjoy home cooked meals! The living room has a wood burning fireplace for crisp and cold evenings.brbrLiving room has a large Smart TV with streaming capabilities. Log onto your streaming apps: Netflix, Hulu, Amazon Prime, etc. There is also a Smart TV in the upstairs bedroom. brbrThere are four (4) total bedrooms to accommodate guests during your stay:brbrMain level primary suite: king size bed with en suite bathroombrUpstairs bedroom 1: one queen size bedbrUpstairs bedroom 2: two twin bedsbrLower level bedroom: one full size bedbrbrThere are three (3) full bathrooms and one half bathroom: Each of the three house levels has a full bathroom. The main level full bathroom is an ensuite to the first floor primary suite The lower level and upstairs bathroom each have a shower, and the primary suite bathroom has a separate tub and shower. There is also a half bath on the main level.brbrOutdoors is where you can truly experience the Berkshires in all seasons. You’ll find a huge 1000+ square foot deck surrounded by magical and mature grape vines and hummingbirds, an outdoor sofa, dining table/chairs, gas grill, lounge chairs, large yard, an outdoor hot tub, and even a fire pit. The deck receives ample morning sunlight; in the evening, enjoy beautiful sunsets behind the house.brbrOther things to note:br-Central AC to keep the house cool during the summerbr-Five stairs to the front door, main level primary suite makes it an easy stay for those with limited mobilitybr-Main level and upstairs have hardwood floors, the lower level is a combination of tile/carpet.br-Parking for 4-6 vehicles in the upper and lower drivewaysbr-Washer/dryer for guests to usebr-Hotel quality linens and towels, as well as shampoo, conditioner and body wash all provided for our guestsbr-The hot tub is serviced frequently and set to 100 degrees by default. As with any hot tub, it will lose heat if the cover is left off for an extended period of time.br-Bring your furry friend, one dog is allowed. $50 per dog per stay. Dogs must be at least one year old, sorry, no puppies!brbrOther Things to Note:brWe look forward to welcoming you soon! brStandard rules apply, including no smoking, no partying, and being respectful of noise levels and our neighbors. br-To gain access to the hot tub, it is necessary for you to sign a waiver specifically designed for its use.br-Guest use of Peloton Bike and Peloton Treadmill is at their own risk. The Peloton Bike and/or Peloton Treadmill may ONLY be used by guests who are 18 years older. Usage by guests under 18 years old is strictly prohibited.brbrNo sweat on accidental & reported damage! 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. br*Not covered by the accidental damage waiver: damage from smoke, damaged caused by pets or any damage to the hot tub.br*Kindly leave garbage inside the bear binbr*Please cover the hot tub correctly and set back to 100 degrees after using.br*Kindly make sure the flue is closed after use. Also the temperatures are correctly set.br-Bring your furry friend, one dog is allowed. $50 per dog per stay. Dogs must be at least one year old, sorry, no puppies!

Beautiful House In The Woods, Huge Yard, Hot Tub

Great Barrington, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$424

Escape to the Berkshires in our newly-restored, cozy-luxe cabin, complete with fireplace, fully-stocked kitchen, high-speed WIFI, comfy linens, heat/AC and tricked-out basement fun room for the kids!brbrOur cabin sits on a secluded 1.5 acres so it feels remote and peaceful, but it's just 3 minutes from Butternut Ski Resort, 1 minute to hiking the Appalachian Trail, and 7 minutes from downtown Great Barrington with its shops, restaurants and theaters. Just 15 more minutes to Stockbridge and Lenox!brThe space:brThe entire cabin is yours to use, and it sits on an acre and a half of secluded, wooded land that is just a five minute drive from everything and anything you might want to do!brGuest accessbrGuests have access to the entire cabin, which includes free laundry in the basement.

Cabin

Luxe Log Cabin Minutes From Skiing, Hiking, & More

Great Barrington, Massachusetts, United States

Bed

2

Bath

10

Sleeps

$196

Located in Great Barrington, this superb house boasts 3 cozy bedrooms - one with a king bed, one with two twin beds, and one with a queen bed. With amenities like heating, AC, WiFi, and a washer/dryer, guests can relax in comfort. The property also features 3 bathrooms with a bathtub and/or shower. Make your holiday one for the books with a stay at our home.

Large 3-bedroom house with WiFi and AC in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$663

We are thrilled to share our country escape with you and hope you enjoy it as much as we do. Set on 5 acres of land, with an open backyard with a trampoline and trees surrounding you, our fully stocked home is true escape from the busy, over scheduled days of city life. We are a few minutes away from many wonderful, scenic hikes, a few breathtaking swimming lakes and skiing in the winter. Warm up by the fireplace after a long day outdoors or turn on the bbq for a delicious outdoor meal on the porch.

Cozy escape in the trees of the Berkshires

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$338

Bagels & Slopes: Start Your Day Deliciously, Hit the Powder Perfectly!brbrWelcome to the ultimate ski getaway where comfort, convenience, and a touch of indulgence await! Begin your morning with complimentary fresh bagels & coffee from our favorite local neighborhood bagel shop - mere steps from your front door. Then, hit the slopes at a nearby ski resort, with Butternut just 7 minutes away and Catamount only 12.brbrBagels: The Great Barrington Bagel Company is just two doors down from the house and is a must-stop for all guests visiting the Berkshires, regardless of where you stay! We have partnered with the Bagel Shop to offer a complimentary breakfast bagel sandwich and hot beverage to every guest on the reservation during your stay! brbrSki/Snowboard: During the winter season, we are excited to also offer one complimentary lift ticket to a local ski resort for any stay longer than 7 nights! brbrHost: As someone who was born and raised in the Berkshires, I am so happy to have the opportunity to show my guests the best my hometown has to offer - bagels and skiing is just the start! Because we are local, we are just a text/call and short drive away, so can help with anything that may come up during your stay. Having a local host can elevate a lot of the unnecessary stress on your vacation. We aren't some big corporate company and we are so happy to help! brbrHouse: This newly renovated 3-bedroom, 2-bathroom house in Great Barrington is perfect for families and groups of up to 6 guests. It offers a cozy yet modern retreat with all amenities. The primary bedroom on the first floor has a king bed and an en-suite bathroom. The two upstairs bedrooms each have queen beds and share a connecting bathroom. One of the upstairs bedrooms includes a work desk, perfect for those needing to catch up on emails or enjoy some quiet reading time. The kitchen is fully stocked and includes a dishwasher, microwave, fridge, stove, oven, and everything you need to cook. It's connected to a cozy living room with a comfortable couch, smart TV, board games, and playing cards. Lastly, enjoy the brand new large back porch with a Weber Grill and outdoor seating.brbrCome check us out and let us know if you have any questions!brShoe free house

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

Great Barrington, Massachusetts, United States

Bed

2

Bath

6

Sleeps

$439

Perfect Berkshire getaway. Minutes from downtown Great Barrington and Stockbridge, Tanglewood, Rockwell Museum, multiple ski areas (Butternut, Catamount, Bousquet, Otis). Located in Great Barrington a short drive from shops and restaurants. brWe will offer better pricing for those who would like to book the entire summer season. Please inquire directly.

Berkshire Cottage - seasonal rentals highly encouraged!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$451

Guests can take in the view from the front porch, and the house has plenty of space, including the basement game room and the backyard. The house has everything you need to enjoy Great Barrington. You are only one mile from the main street and the shops, restaurants, and bars.brbrThe large great room has seating for eight, a TV, and plenty of board games and puzzles. After a day of exploring the Berkshires, you can enjoy watching TV in front of the fireplace. There is a smart TV, so you can connect your streaming apps to enjoy your shows. You can also snuggle up under a blanket while enjoying the propane fire table on the front porch. The well-stocked kitchen has stainless steel appliances, granite countertops, and gas cooking. It also has all the necessary appliances plus a dishwasher, making cleaning up a breeze.brbrThe kitchen has all the cooking/serving necessities, including cookware, pots, pans, plates, cups, and silverware. There's also a waffle maker, blender, panini press, hand blender, and drip coffee pot for your morning coffee.brbrThe dining room table seats 6, and the bar counter seats another 4.brbrThere are 2.5 bathrooms: one upstairs has a tub/shower, the master bath has a shower, and the lower level has a half bath.brbrTo help you with sleeping arrangements:brBedroom 1: upstairs level, 1 queen size bed, and a full size fold out sofa bedbrBedroom 2: upstairs level, 1 queen size bedbrBedroom 3: upstairs level, 1 queen size bedbrbrOne of the bedrooms can also accommodate a twin-size inflatable mattress, a Pack and Play, or an Inflatable Toddler Travel Bed with Safety Bumpers in addition to the queen-size bed. The photos show the possible layouts. brbrOther amenities worth noting:br- The second-floor bedroom has workout equipment, including a Peloton bike, yoga mat, blocks, and 3, 5, and 8-pound hand weights.br- The basement has a ping pong table and a smart TV with a game console. br- Central heating and air conditioning.br- Laundry machine available.br- Fireplace in the great room ready to make cozy fires after a day of skiing - firewood provided. br- Wifi throughout the house.br- Parking for up to 2 cars in the driveway.brbrTanglewood and Beach supplies for your convenience:brCooler, ice packs, towels, folding chairs, beach bag, picnic blanket, portable table, wagon, and more. brbrBaby Gear:brAll baby gear is thoroughly cleaned and in like-new condition. Please let us know if you would like to use any of these items. Baby gear includes:brbrHiccapop inflatable Toddler Travel Bed with Safety Bumpers, sheets, and blankets. Sleeping Area Dimensions: 49 x 26 inchesbrbrGraco Pack 'n Play On the Go Playard has sheets, a waterproof pad, a blanket, and a toddler pillow.brbrInglesina Fast Table Chair (This is a chair that is clipped onto the table.)brbrHelloBaby video monitor HB6550pro, 5''Sreen with Pan-Tilt-Zoom and Audio, Night Vision, VOX, 2-Way TalkbrbrBaby bath seat- Delight Cushy Nest Cloud Premium Organic Infant Bather brbrBaby Body Wash & Shampoo.brbrBaby safety supplies include outlet covers, corner guards, stove knob covers, and door knob covers.

Contemporary 3-bedroom home with views, fireplace & close to Butternut Ski area

Great Barrington, Massachusetts, United States

Bed

About this spacebrWelcome to the Berkshires!!! A very large duplex apartment with own entrance and a porch to relax in. This is all within walking distance to town. This roomy space features a country décor with a cozy, homey feeling that has a bathtub upstairs and a shower stall downstairs. Easy access to all favorite places like Tanglewood, Norman Rockwell Museum and Bash Bish Falls to name a few. There are some nice restaurants, many antique stores and hiking, like up Monument Mountain.brThe spacebrYou will have the entire apartment to yourself. The front door leads into your own cozy porch. There is no interaction with back apartment tenants, who are quiet. There is ample parking space.brGuest accessbrGuests have full access to entire space for themselves.brOther things to notebrThe bedroom situation is such that you have to walk past first opened bedroom to get to the other bedroom and bathroom. The second bedroom has a door.brThe upstairs bathroom has a tub, which there is also a wand for rinsing off. It is not very tall inside tub, so it would be hard to take a shower in it if you are over 5’3”. There is a shower stall in the first floor bathroom though.

Bath

6

Sleeps

Select Dates for Price

Apartment

Eastbungalow

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$3,774

A breathtaking estate nestled on a mountain slope of granite in the Berkshires. Immerse yourself in 120 acres of natural wonders & wildlife. A private oasis that delivers inner peace & rejuvenation. brMain house: 9 bedrooms and 8 bathsbrGuest house: 2 bedrooms and 1 bath (extra cost)brBarn: 3000 sq ft (extra cost)br* 11.7% MA state tax paid by guestbrThe spacebrPricing and capacity:brPricing on this site is for main house up to 14 people. The entire property which is 11K square foot includes 7 bedrooms in the main house with 3 additional private rooms that can easily be converted to bedrooms. We also have a guest house on the property with 2 bedrooms, a full bath and a living room and kitchenette and a 3,000 square foot barn which has a lounge/ loft, kitchen, 2 showers, washer and dryer, a basketball hoop and ping pong table. The barn and guest house are rented separately, so you have the choice to rent them all or just rent the main house.brbrA vacation paradise for all seasons, long pond 250 has it all. If you are looking for a winter holiday, long pond is a short 15 min drive to the kid friendly butternut and Catamount ski resorts. After a day of skiing (or in lieu of), retreat to our oasis in the mountains and enjoy sledding on the property, sip hot chocolate and barbecue marshmallows around our beautiful firepit and end the evenings by cooking in our chef inspired kitchen with a glass of wine by one of the indoor fireplaces. Don't forget to top it off with a quick dip in the hot tub on the porch in the summer or winter! If you are looking for some downtime and don't feel like being in the kitchen or cleaning, we have a host of wonderful local chefs and service providers in the area.brbrIn the summer, the pool is wonderful, the surrounding area lush and green. We have hiking trails on the property, bikes for those that want to get in some exercise and tubes for the pool.The pool and hot tub are closed from September to May. brbrHot tub is extra $600 charge as it needs to be cleaned and prepped between guests.brGuest accessbrThere are several dwellings on the property as well as 120 acres. Inquire about what is included.brbrParties and eventsbrUntil further notice, all disruptive parties and large events are prohibited regardless of size.

Magical Country Retreat in the Berkshires

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$245

Berkshire Mountain Cottage is a warm and cozy hideaway located in the Berkshire hills. Its located between North Egremont and West Stockbridge, placing it within 15 minutes of Tanglewood and 5 minutes from Main Street in Great Barrington, by car, and close to many other Berkshire locales. The cottage is also very close to hiking and biking trails and numerous swimming areas on both lakes and rivers.brbrThe cottage features (2) bedrooms, living room, kitchenette, screened in porch and (1) bathroom. The master bedroom contains a Queen sized bed and plenty of closet space. The second bedroom has a trundle bed with a riser and it sleeps (2). The building is semi attached to the main house. It has a separate entrance. And private outdoor area It is a roomy 800 sq ft, recently renovated, and beautifully decorated. You can easily prepare a great breakfast, lunch and even dinner (BBQ) or choose to sample one of the many restaurants in Great Barrington.brbrThe cottage property contains grassy areas, flower gardens, forest, a stream, and a beaver pond which attracts exotic birds. There are tables and chairs set up outdoors for your enjoyment. We welcome well behaved dogs of all sizes. brbrIn these special days we are taking special measures to keep everyone healthy.brAll guest reservations are spaced 1-3 days apart when possible, to allow airing, and cleaningbrWe take special care of cleaning and sanitizing the cottage prior to your arrival.brAll linen and towels are washed at a high temperature, and dried in high heat. brWe change all linen, including duvet cover for each guest (European style).brCleaning is conducted with masks and gloves.brbrbrbrKeywords: Cottage

Cottage

Berkshire Mountain Cottage: in the Heart of the Berkshires

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$443

Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This rustic 4-bed, 2-bath home is complete with woodsy-style decor, contemporary furnishings, and space for 10. It's truly a sportsman's paradise - tucked away in the woods on Round Pond, where you can hike, fish, swim, boat, or admire it all from the deck and dock. Whether you're here for summers at the Symphony, winters on Ski Butternut, or leaf peeping in the fall, Great Barrington has it all.brbr-- THE PROPERTY --brbrBedroom 1: Full Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed | Bedroom 4 (Loft): Twin Bed with Twin Pullout (Can be converted into a King), Full BedbrbrYou'll find this rustic property hidden away in a semi-remote, wooded area, with very few neighbors nearby. Mornings here offer incredible views and quiet surroundings - best enjoyed with a warm cup of coffee on the deck.brbrThis property is located right on Round Pond. With crystal clear water untouched by busy beaches or motor boats, this lake is ideal for swimming and fishing! Take a dip off the dock, or venture out on the rowboat provided.brbrAfter a day on the lake, head inside to enjoy some downtime. The living room is complete with cathedral ceilings, floor-to-ceiling views, and a cozy wood-burning fireplace, altogether creating the perfect place to unwind.brbrEnd the day with a hearty meal made in the fully-equipped kitchen. Follow dinner with a sweet treat of s'mores by the outdoor fire pit!brbrWhen you're ready to retire for the night, 4 bedrooms offer space for up to 10 guests.brbr-- THE LOCATION --brbrNamed as the #1 best place to live by Smithsonian Magazine, Great Barrington is a small-but-mighty town brimming with activities and charm.brbrTake some time to tour the Berkshires. Within 15 minutes you'll be able to hike across Monument Mountain, shop and dine in Great Barrington, stop by the Norman Rockwell Museum in Stockbridge, or test your winning streak at the Springfield Casino just 40 minutes away.brbrThe famous Tanglewood lies just 10 miles away. Since 1937, Tanglewood has served as the summer home for the Boston Symphony Orchestra. Concerts here will take your breath away!brbrThe Berkshires turn into a winter wonderland when the snow falls. You'll find multiple mountains within 10 minutes of the property, including Ski Butternut and Catamount Ski Area, with Bousquet Ski Area, Jiminy Peak, and more just a short drive further!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- Massachusetts Tax ID: C0198611130br- No smokingbr- Pet friendly with $75 per stay fee (dogs only)br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There is a completely separate unit located next door with its own private entrance. Other guests will not be present however the separate unit is off limitsbr- NOTE: This unit also has exterior-facing cameras, but they do not look into any interior spaces of the vacation rentalbr- NOTE: The property requires stairs to accessbr- NOTE: The property does not have air conditioning

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$177

Historic home Nestled on a quiet street in downdown Great Barrington, just steps from the River Walk path, this enchanting apartment features 2 bright and airy queen bedrooms, perfect for a small group of guests. brbrThis is a Duplex house - you will have one entire side which has a queen bedroom on the first floor and a Queen bedroom and bathroom on the second floor. The stairs to the second floor have a handrail but they are steep. The apartment features amenities like Roku TV, WiFi, Back Yard Gas Grill, washer/dryer in Basement, fully equipped eat-in kitchen. brbrThe apartment has beautiful artwork throughout and nice touches like plants and locally made pottery. The newly renovated bathroom offers modern glass door, step-in shower.brbrThe font enclosed porch is perfect for storing ski or outdoor gearbrbrYour stay will be comfortable and convenient as you can easily walk to the downtown cafes, food coop, great restaurants and the theater. We are a 10 minute drive to Butternut ski areas and close to hiking trails and performing arts center - Tanglewood and Jacobs Pillow. brbrWe hope you enjoy what our place and everything the Berkshires and Great Barrington has to offer.

Apartment

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$399

CATAMOUNT SKI RESORT IS ON THE OTHER SIDE OF THE MOUNTAIN. 11 MILES TO SKI BUTTERNUT.brHIGH SPEED FIBER OPTIC INTERNET brbrOur vacation home is built into a steep, secluded, forested mountainside, near the village of South Egremont. It is a short distance from all the wonderful attractions located in Berkshire County, as well as Columbia County in New York -the heart of the Hudson Valley (only 1 mile over the mountain), and Litchfield County, Connecticut (only a 10 mile drive). There is no light pollution, and other than the sounds of nature, it is so quiet at night you can hear the beating of your heart. The house has two large decks and a smaller side deck that provide great views of the surrounding countryside. The only likely neighborhood residents you will see (we have) include bear, deer, moose, fox, eagles, hawks, ravens, and numerous owls. brTimberdoodle is close to many of the attractions for which the Berkshires of Western Massachusetts are noted for. It is five minutes away from one of the best restaurants in Berkshire County-the Old Mill. Hiking, skiing and other outdoor recreation are within 10 minutes of our vacation home, including the Appalachian and South Taconic Trails, the Jug End State Reservation, and Bash Bish Falls-the State's highest. The picturesque town and local commercial hub of Great Barrington is only a 7 mile drive. The house is only 21 miles from the famous Tanglewood Music Center, the summer home of the Boston Symphony Orchestra. Nearby cultural venues abound, including Jacob's Pillow Dance Center, Shakespeare & Company, the Mahaiwe Performing Arts Center, and the Colonial Theater.brThe kitchen, although compact, has all the appliances and equipment necessary to make fantastic meals from the locally raised and grown food that you can obtain at the many farmer's markets in the area. All essentials are included, such as towels, bed sheets, soap, toilet paper and pillows. There are fully stocked pantry shelves including coffee beans, essential kitchen staples, condiments and dry goods. The kitchen includes a Kitchen Aid ceramic top convection range, Bosch dishwasher and Fisher Paykel french door refrigerator/freezer. The kitchen inventory includes a Breville toaster, Panasonic combination microwave, steamer and convection oven, Vorwerk Thermomix (a German blender on steroids), an Instant Pot, Cuisinart food processor, Baratza Coffee Grinder, and a Technivorm drip coffee maker. The kitchen has been provisioned with fine kitchenware including from Cristel, Le Crueset, Mauviel, Finex, Wusthof and ScanPan. The upper deck contains a gas grill, and a Blaze Kamado-style charcoal grill is located in front of the house near the lower deck. For in-home entertainment, the living room has a 4K high definition television connected to a Dish satellite receiver. Both this television and the one located in the large top-floor bedroom are connected to internet streaming services provided by Roku boxes. We have no air conditioners. Because of the cool mountain air and the 1300 feet elevation, we only occasionally use the provided fans on the hottest Summer days.brTwo of the bedrooms have queen beds and the third bedroom has two twin beds.brbr25% DISCOUNT FOR 28 OR MORE NIGHTS. THE RENTAL QUOTE VRBO PROVIDES WILL AUTOMATICALLY INCLUDE THE DISCOUNTED RATE.

Timberdoodle-a mountainside treehouse

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$1,064

In 2016 Smithsonian Magazine deemed Great Barrington, The Best Small Town in America. Manor Lane is a private French Country Estate located only 5 minutes from the heart of the Berkshires. Situated 10 minutes to both Butternut and Catamount ski mountains and 25 minutes to Tanglewood. brManor Lane is a private Estate where each room has been endowed with notable charm. A French Manor House with private pool and tennis court, formal living and dining rooms, fireplace, study and unique Gauguin Bar. The house has welcomed numerous noteworthy guests along the way including: Donovan, Roger McGuinn and Leslie Gore, jazz artists; Bobby Watson, John Hicks and Victor Lewis. brSettle into the relaxing tempo of Manor Lane and let us indulge you with the kind of thoughtful extras that we take pleasure in providing.

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$470

Newly renovated 4 bedroom and 2 full bath home set back from the road is a peaceful oasis. 2 minute drive to Ski Butternut, 8 minutes to downtown Great Barrington. Vaulted ceilings, heated tile bathroom floors and 2 wood burning stoves and minisplit AC/Heating systems in every room. Gas grill, covered gazebo and a firepit perfect for a year round escape. Child's play structure with two swings and a slide also on premise.

Private Berkshires Getaway Minutes to Ski Butternut

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$693

Main floor bedroom with private bath, 2 car garage, electric vehicle charging, screened porch, pool, and Koi pond with views into Connecticut and also north toward Monument Mountain. Located within 1 mile of downtown Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington, Massachusetts, United States

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