Home Vacation Home Rentals By Owner In Great Barrington, MA

Showing 20 Of 75 Vacation Rentals
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Exceptional(50)

$380.9

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Private Vacation Home

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Great Barrington, Massachusetts, United States

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 w/ $75 fee (+ fees & taxes, dogs only)br- No events, parties, or large gatheringsbr- 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
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Bath 2

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Sleep 10

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Exceptional(58)

$826.58

/ Nightly
Private Vacation Home

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

Great Barrington, Massachusetts, United States

A lovely property with gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood & Jacob's Pillow. 5 bedrooms (6 beds), 3.5 baths, sleeps 12. The 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). Downstairs floor has 2 bedroom (one has attached full bath), and laundary/exercise room. 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.
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Bath 3

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Sleep 10

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Exceptional(1)

$428.18

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Private Vacation Home

Cozy Great Barrington Cottage with Mountain View

Great Barrington, Massachusetts, United States

Welcome to our cozy Great Barrington cottage with views of Butternut Mountain! Less than a 5-minute drive to downtown Great Barrington, where you will be able to explore local shops and great restaurants. Walking distance to supermarkets, restaurants, and so much more. A short drive to all major activities including 5 minutes to Ski Butternut, 15 minutes to Catamount, and 20 minutes to Tanglewood. Centrally located to all the Berkshires has to offer!brbrRecently updated with TLC, the cottage provides a cozy Berkshire experience for you and your family or friends. Walk into the cottage through the stone mudroom and enter the kitchen, which has been newly painted, includes new appliances, and is fully equipped. Continue walking through to the dining room where you will find a handmade custom farm table where you can eat drink and chat. After the dining room is the comfy living room where you will have access to a smart TV with streaming capabilities. The bathroom is newly renovated and features a barn door and a subway tile shower. Downstairs are two bedrooms, one with a queen bed and the other with a full bed, both with views of Butternut Mountain. Upstairs has one queen bedroom and a BRAND NEW (2023) extension, featuring a tiled bathroom with rain shower, standalone soaking tub, and heated floors, and a fourth bedroom containing a twin bed, mini crib, and changing table. Mini crib has the comfortable Newton breathable mattress. Upstairs bedroom and bathroom both have mountain views. Original but re-finished wood floors throughout the entire cottage. Take a walk out back where you can BBQ on our pea gravel patio or sit around the fire pit in our Adirondack chairs and make s'mores. The property is completed fenced. Enjoy the Butternut Mountain View. The cottage has high-speed WiFi and a designated work space. Perfect for a family or a few friends to get away and explore all the Berkshires has to offer.brbrParking for up to four cars. Dogs allowed upon pre-approval.
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Bath 2

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Sleep 7

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Exceptional(10)

$691.42

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Private Vacation Home

Butternut Ski Retreat - Fireplace, Views and close to town!

Great Barrington, Massachusetts, United States

This contemporary, light-filled 3BR, 2.5BA home is less than a mile from Lake Mansfield and downtown Great Barrington, with easy access to shops, cafés, trails, and museums. Take a short drive to Lenox, Stockbridge, or Hudson. Relax on the porch with coffee or wine while enjoying views of Butternut Mountain.brbrInside, you’ll find a fully stocked kitchen, wood-burning fireplace, board games, a basement with ping pong, a Smart TV, and a spacious yard—perfect for your Berkshires retreat. The basement game room and large backyard offer plenty of space for everyone. Butternut ski area is just seven minutes away for winter fun.brbrThe spacious great room offers comfortable seating for six, a Smart TV, and a Bluetooth sound system integrated into the walls and ceiling for an immersive experience. After a day of exploring the Berkshires, unwind in front of the fireplace while enjoying your favorite shows via your streaming apps on the TV. For music lovers, the built-in Bluetooth speaker system lets you easily connect your phone and play your favorite tunes. Plus, with plenty of board games and puzzles, there’s entertainment for everyone.brbrThe fully equipped kitchen boasts stainless steel appliances, granite countertops, and a gas stove, making meal prep easy and enjoyable. You'll find all the essentials for cooking and serving, including cookware, pots, pans, dishes, glassware, and silverware. We’ve also included a waffle maker, blender, panini press, hand blender, and a drip coffee maker to start your mornings right.brbrThe dining area comfortably seats six at the main table, with additional seating for four at the bar counter—perfect for family meals or casual gatherings.brbrThe home features 2.5 bathrooms: the upstairs bath includes a tub/shower combo, the master ensuite has a walk-in shower, and a convenient half bath on the lower level.brbrpstrongSleeping Arrangements:/strong/pbrulbr listrongBedroom 1:/strong Upstairs level, featuring a king-size bed and a full-size fold-out sofa bed./libr listrongBedroom 2:/strong Upstairs level, with a queen-size bed and a queen-size fold-out futon./libr listrongBedroom 3:/strong Upstairs level, furnished with a queen-size bed./libr/ulbrOne of the bedrooms can accommodate a Pack and Play, or an inflatable toddler travel bed with safety bumpers. The listing photos display the possible layout options.brbrOther notable amenities include:brulbr listrongA ping pong table/strong and strongsmart TV/strong with a stronggame console/strong in the basement./libr listrongCentral heating/strong and strongair conditioning/strong for year-round comfort./libr listrongOn-site laundry facilities/strong./libr listrongA cozy fireplace/strong in the great room, perfect for unwinding after a day of skiing (strongfirewood provided/strong)./libr listrongA propane fire table/strong on the front porch with strongscenic views/strong—ideal for relaxing outdoors./libr listrongWiFi/strong available throughout the house./libr listrongParking for up to 2 cars/strong in the driveway./libr/ulbrBeach/Tanglewood supplies:brulbr listrongCooler/strong with ice packs to keep your drinks and snacks cool./libr listrongBeach Towels/strong for a relaxing day by the water./libr listrongFolding Chairs/strong for comfort and convenience./libr listrongBeach Bag/strong to carry all your essentials./libr listrongPicnic Blanket/strong for enjoying meals outdoors./libr listrongPortable Table/strong for extra convenience during your outings./libr listrongWagon/strong to easily transport your items to the beach or park./libr liAnd more, to ensure a hassle-free and enjoyable experience./libr/ulbrThe house is NOT baby-proofed, but we do have some baby supplies to simplify your travels: brulbr listrongHiccapop Inflatable Toddler Travel Bed/strong with Safety Bumpers, sheets, and blankets. Sleeping area dimensions: 49 x 26 inches./libr listrong(2) Graco Pack 'n Play On-the-Go Playards/strong with optional bassinet attachment, sheets, a waterproof pad, blanket, and toddler pillow./libr listrongInglesina Fast Table Chair/strong (clips onto the table for easy seating). /libr listrongINFANS High Chair/strong for babies and toddlers, foldable with adjustable backrest, footrest, seat height, and removable tray./libr listrongMaxi-Cosi Rocker/strong for comfortable rocking and soothing./libr listrongHelloBaby Video Monitor HB6550pro/strong, 5-inch screen with pan-tilt-zoom, night vision, VOX, and two-way audio./libr listrongDreamegg White Noise Machine/strong to help soothe your baby to sleep./libr listrongBaby Body Wash & Shampoo/strong, gentle and safe for your little one’s sensitive skin./libr listrongBaby Safety Supplies/strong including outlet covers, corner guards, stove knob covers, and door knob covers for extra peace of mind./libr/ul For stays shorter than 31 days, Massachusetts imposes a 5.7% room occupancy tax, and the town of Great Barrington adds 6%, bringing the total tax to 11.7%. Platforms like VRBO automatically collect this tax for stays under 31 days. The good news Stay 31 days or more, and you’re exempt from this tax, saving you 11.7%! Plus, we offer a 5% discount on monthly stays or longer.brbrThe house is in a peaceful neighborhood, so we kindly ask guests to follow standard house rules: no smoking, no parties, and please respect our neighbors.brbrWe provide one propane tank for the BBQ grill or the propane fire table—just let us know in advance if you'd like to use one so we can have it ready for you. Please note that any refills during your stay are the guest’s responsibility.brbrWe look forward to hosting you soon!brbrNearby Attractions & LandmarksbrDiscover top Berkshires destinations just minutes away:brbrGreat Barrington Library (0.9 mi / 3 min): Cozy local library with events and reading rooms.brbrSoCo Creamery (1.4 mi / 4 min): Award-winning, locally made ice cream.brbrTaft Farms (1.7 mi / 5 min): Farm store with fresh produce, baked goods, and seasonal fun.brbrButternut Ski Area (2.6 mi / 7 min): Great for skiing or summer mountain activities.brbrMonument Mountain (4.3 mi / 8 min): Scenic hikes and panoramic views.brbrNorman Rockwell Museum (4.8 mi / 13 min): Celebrate an American art icon.brbrRed Lion Inn, Stockbridge (5.5 mi / 13 min): This historic inn has dining and New England charm.brbrCatamount Mountain Resort (8.9 mi / 17 min): Ski, zipline, or ride the chairlift.brbrTanglewood (12 mi / 20 min): World-class summer music, home to the BSO.
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Bath 2

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Sleep 6

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Exceptional(8)

$3773.86

/ Nightly
Private Vacation Home

Magical Country Retreat in the Berkshires, 10min from ski slopes.

Great Barrington, Massachusetts, United States

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: 7 bedrooms and 8 baths plus 3 private rooms that can be converted into luxurious bedrooms for a small feebrGuest house: 2 bedrooms and 1 bath (extra cost)brBarn: 3000 sq ft (extra cost)br* 14.75% 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 spring or fall! 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/mountain biking trails on the property, and can arrange mountain bike rentals. 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.
Bed 10

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Bath 9

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Sleep 16

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Exceptional(10)

$502.96

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Private Vacation Home

Modern Escape Near Main Street

Great Barrington, Massachusetts, United States

Summary:brbrEnjoy relaxed, easy living on The Hill in Great Barrington. The home has a bright, welcoming vibe with vaulted ceilings, an open layout, and smooth indoor-outdoor flow. Fresh renovations finished in June 2025 brought new life to both bathrooms and the downstairs bedroom. And don’t miss the brand-new bluestone patio with a propane fire table — a standout spot to kick back, gather, and enjoy the outdoors.brbrbrbrThe Space:brbrYour home for the week was renovated and furnished with a mid-century modern vibe and a touch of whimsy. The house has everything you need for a Great Barrington getaway, just a five-minute walk to Lake Mansfield and ten minutes to downtown shops, restaurants, and bars. Renovations wrapped in June 2025, giving both bathrooms and the downstairs bedroom a fresh new feel. You’ll also get to enjoy a brand-new bluestone patio with a propane fire table, perfect for relaxing after a day in The Berkshires.brbr brbrThe large great room has plenty of seating, a record player, huge tv, board games and a foosball table. Here you can enjoy watching TV after a day of exploring The Berkshires. The TV has plenty of cable channels and is a smart tv so has the ability for you to connect your streaming apps to enjoy your shows. brbr brbrWell stocked galley style kitchen with all new stainless steel appliances, quartz countertops and gas cooking. Well stocked with all the necessary appliances plus a dishwasher, to make cleaning up a breeze. brbr brbrKitchen is stocked with all the cooking/serving necessities including: cookware, pots, pans, plates, cups, and silverware. There's also a rice cooker, waffle maker and a drip coffee pot is available for your morning coffee.brbr brbrTrue dining room with seating for up to 8 of your guests. brbr brbrTwo bathrooms, one upstairs has a tub/shower and one on the lower level has a stand up shower. brbr brbrTo help you with sleeping arrangements: brbrBedroom 1: first level, 1 queen size bedbrbrBedroom 2: first level, 2 queen size bedsbrbrBedroom 3: lower level bedroom, 1 queen size bed brbrQueen sofa bed in the living room and a twin size daybed in the great room. brbr brbrPlenty of outdoor seating for alfresco dining with umbrella and a gas grill provided. brbr brbrOther amenities worth noting: brbr-SPRING 2025-Newly renovated bathrooms and downstairs bedroom brbr-Central heating to keep you warm this winter.brbr-Upstairs bedrooms have recently installed rugs, lower level bedroom has recently installed plank flooring. The remainder of the house has hardwood floors.brbr-Bring your furry friends, up to 2 dogs allowed, up to 50 pound limit and its $50 per pet per stay. No other animals allowed due to allergies. brbr-Laundry machines available.brbr-Two stairs to the front door where most of the house is, about 10 stairs down to the lower level bedroom.brbr-Fireplace in the great room ready to make cozy fires. brbr-Fast wifi throughout the house.brbr-Beautiful wood paneling and trim in living and dining rooms.brbr-Kids will love the Pacman mini arcade game. brbr-Parking for up to 4 medium size cars in the driveway.brbr-There is a tenant who lives in an apartment which is attached to the house. They have their own entrance and will not affect your stay.brbr-Picnic supplies available; insulated picnic basket, portable snack table and outdoor blanket.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, and more!brbrbrbrThe Neighborhood:brbrShort 5 minute stroll to Lake Mansfield for swimming! brbrbrbrWALKING distance to downtown and all the great restaurants/shops that Great Barrington has to offer. brbrbrbrOther area attractions: brbr5 minute drive to Ski Butternutbrbr20 minutes to Tanglewoodbrbr15 minutes to Lenoxbrbr10 minutes to Stockbridgebrbrbrbr20 minutes to Catamount Skiingbrbr30 minutes to Jocobs pillowbrbr25 minutes to Bish Bash Fallsbrbr20 minutes to Becket hiking areabrbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brbrBring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrbrbrNo 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.brbr*Damage caused by pets is not covered by the accidental damage waiver.
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Bath 2

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Exceptional(1)

$848.9

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Private Vacation Home

Historic, Modern Comforts, Walk To Downtown

Great Barrington, Massachusetts, United States

Summary:brbrSpacious historic home in Downtown Great Barrington blending century-old charm with modern comforts. Sleeps up to 16 with well-appointed bedrooms, a cozy dining room with fireplace, and a fully equipped kitchen. Enjoy central heat/AC, high-speed Wi-Fi, and a fenced backyard with seating and BBQ. Just a 5-minute walk to downtown, this former mill manager’s house offers the perfect Berkshires getaway for families and groups.brbrbrbrThe Space:brbrStep into this spacious five-bedroom, three-bathroom home that perfectly blends historic character with modern comfort. Originally built in the early 1900s as the mill manager’s house for the nearby riverfront mill, it retains its century-old charm while offering every modern amenity you need for a relaxing stay in the Berkshires. With sleeping space for up to sixteen guests, the home features a thoughtful layout: one bedroom with a queen bed, another with two queens, a third with a queen, a fourth with two full beds, and a fifth with a queen and desk, along with a pullout sofa in the living room. Bedrooms one through three include ceiling fans for added comfort. brbrbrbrEach floor has a full bathroom. On the first floor, a rain shower with heated floors; on the second, a tub/shower combo with both showerhead and handheld sprayer; and on the third, a shower with rain shower and handheld features.brbrbrbrFor easy planning, here are the bedroom layouts:brbrBedroom 1: Queen BedbrbrBedroom 2: Two Queen BedsbrbrBedroom 3: Queen BedbrbrBedroom 4: Two Full BedsbrbrBedroom 5: Queen Bed + DeskbrbrLiving Room: Queen Sofa BedbrbrbrbrThe inviting living room provides a comfortable gathering space for groups of all sizes. With ample seating and a pullout sofa, it’s perfect for relaxing after a day exploring the Berkshires. Large windows fill the room with natural light, while tasteful furnishings and cozy accents create a welcoming atmosphere. A Smart TV allows you to log into your favorite streaming apps, making it easy to enjoy a movie night or catch up on shows during your stay.brbrbrbrThe eat-in kitchen includes seating for six, new appliances, a deep sink with commercial-style faucet, and an electric range. A dining table for eight and a kitchen bar with six seats provide plenty of room for meals, and a drip coffee maker is available for morning routines. The dining room, with its wood-burning fireplace, offers a cozy gathering space, while the home’s hardwood floors, rugs, and mix of antiques and eclectic furnishings create a warm and inviting atmosphere. Modern conveniences include full heating and air conditioning with individual controls for each room, plus high-speed internet supported by mesh networking that even extends into the yard.brbrbrbrOutside, a fully fenced backyard offers seating for eight and a gas BBQ grill, perfect for outdoor dining. Parking for up to five vehicles is provided, with additional street parking available. Situated just across from the river and only a five-minute walk to downtown Great Barrington, the home places you close to shopping, dining, cultural attractions, and all the natural beauty the Berkshires have to offer.brbrbrbrOther things to get excited about:brbr-The house has full heating and central air conditioning with controls for each roombrbr-Washer and dryer for your use.brbr-4 steps to the front door w/ common area sleeping arrangements on the main floorbrbr-Curbless shower in the first floor full bathroombrbr-Ample parking for 5 cars and street parking available brbr-Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies. Your furry friend will appreciate the fully fenced in yard! 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 to downtown and all the great restaurants/shops that Great Barrington has to offer. 350 feet from the front door.brbrbrbrWalk to hiking trails and lakes from the house or take a quick 5-10 minute drive to many more hiking trails in the mountains and lakes.brbrbrbr20 minutes to Tanglewoodbrbrbrbr15 minutes to Lenoxbrbrbrbr10 minutes to Stockbridgebrbrbrbr5 minute drive to Ski Butternutbrbrbrbr20 minutes to Catamount Skiingbrbrbrbr30 minutes to Jocobs pillowbrbrbrbr25 minutes to Bish Bash Fallsbrbrbrbr20 minutes to Becket hiking areabrbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! Standard rules like no smoking, no partying, and being respectful of the neighbors apply. Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies! brbrbrbrNo 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. Pets: Damage caused by pets is not covered by the accidental damage waiver.
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Exceptional(13)

$396.36

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Private Vacation Home

Timberdoodle-a mountainside retreat

Great Barrington, Massachusetts, United States

CATAMOUNT SKI RESORT IS SEVEN MINUTES AWAY. 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.brbrA SUBSTANTIAL DISCOUNT IS AVAILABLE FOR SEASONAL RENTALS
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Sleep 6

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Exceptional(2)

$610.64

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Private Vacation Home

3-Bedroom Victorian home within walking distance of downtown Great Barrington.

Great Barrington, Massachusetts, United States

Higgins House: A 1920 Folk Victorian Retreat Close to the Town CenterbrbrWelcome to Higgins House, a beautifully restored Queen Anne Folk Victorian cottage built in 1920 and set 100 feet off the road in its own quiet, private setting. Located just a short stroll to downtown Great Barrington, Lake Mansfield, and Berkshire trailheads, this home blends historic charm with thoughtful, newly renovated comfort — the ideal retreat for families, couples, and culture-seekers alike.brbrFlooded with all-day sunlight and surrounded by mature trees, this Berkshire gem is designed for slow mornings, long dinners, and cozy evenings viewed through the lens of nature.brThe SpacebrHiggins House honors its Folk Victorian roots with original clapboard siding, cedar shakes, and a charming enclosed porch — classic New England character softened by warm, modern interiors. Inside, intentional design choices, natural materials, and curated color palettes give the home its distinctive sense of place.brFarm Kitchen & Living SpacesbrThe heart of the home is the kitchen, featuring:br • A charming breakfast nook and farm-style island. br • A gas stove with range hood, microwave, and quiet dishwasherbr • Sunlight pouring in from morning to afternoonbrbrBeyond the kitchen sits a warm, relaxed dining room and a double parlor complete with comfortable sofas and accent chairs, and a large smart TV streaming access to all popular entertainment channels. brbrMultiple seating zones allow one group to watch TV while others play games or chat in the adjacent lounge — connected but not crowded.brBedrooms (Sleeps 6 Comfortably)brHiggins House offers three spacious bedrooms, each with high-end memory foam mattresses, cotton sheets, down-alternative duvets, and four pillows per bed.brBedroom 1 – Main Suitebr • Queen bed (high-end memory foam)br • Streaming-enabled TVbrBedroom 2br • One queen bedbr • 12-inch memory foam mattressbrBedroom 3br • One queen bedbr • 12-inch memory foam mattressbrbrThe layout is ideal for families, multi-couple travel, small retreats, and visiting friends of the Berkshires.brBathroomsbrYou’ll find 2.5 bathrooms, all newly renovated:br • Full Bathroom 1: Shower with excellent water pressurebr • Full Bathroom 2: Shower/tub combo with rain shower head + handheld sprayerbr • Half Bath: Conveniently located for shared livingbrOutdoor LivingbrHiggins House is designed for following sunlight throughout the day:br • Morning: Enjoy coffee in the front porch as the sun rises over East Mountainbr • Afternoon: Move to patio to enjoy the beautifully designed goshen-stone patiobr • Evening: Consider grilling outside and enjoying the quiet hillside brUnbeatable LocationbrEverything is at your fingertips:br • 10- minute walk to restaurants, cafés, and shops of downtown Great Barringtonbr • 5 minutes to Ski Butternutbr • 15 minutes to Catamountbr • 20 minutes to Tanglewoodbr • Short drive p to Lake Mansfield — swimming, a lifeguarded beach (seasonal), picnic areas, fishing, and a flat walking trailbrAmenitiesbr • Central heatingbr • Mini splits units in every bedroom, the living room, and kitchenbr • Fast, reliable WiFibr • Laundry in basement with washer & dryer (detergent provided)br • White oak floors in living spaces; exposed wide pine floors and rugs in bedroomsbr • Parking for up to 4 carsbr • Luxury linens, towels, hairdryer, iron + ironing boardbr • Smart TV with atteamung appsbrEverything is set up to help you relax from the moment you arrive.brWhy Guests Love Higgins Housebr • A 1920s Queen Ann Victorian home with newly renovated comfortsbr • Peaceful hilltop setting with mountain and treetop viewsbr • Walkable to town, swimming, dining, and hikingbr • Perfect for families and groups seeking space, style, and serenitybr • Designed with warmth, attention to detail, and an unmistakable Berkshire spirit
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Bath 2

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Exceptional(8)

$635.3

/ Nightly
Private Vacation Home

Perfect Nature Haven In Great Barrington

Great Barrington, Massachusetts, United States

Summary:brbrWelcome to your home for the week in Great Barrington—a spacious, nature-surrounded retreat. Just a 2-minute drive or 15-minute walk to downtown GB. Your stay includes three bedrooms and three bathrooms, accommodating up to eight guests. Highlights include a primary suite with a jetted tub, al fresco dining on the deck, a ping pong table, and more! Experience comfort, convenience, and natural beauty in this serene getaway.brbrbrbrThe Space:brbrWelcome to your spacious retreat in the heart of Great Barrington. This comfortable home features 3 bedrooms and 3 full bathrooms, accommodating up to 8 guests. The upstairs primary suite boasts a king-sized bed, walk-in closet, and an ensuite bathroom with his-and-her sinks, a jetted tub, and a walk-in shower with a skylight. The upstairs guest room also has a king-sized bed, closet, and an ensuite bathroom with a walk-in shower featuring a skylight. The downstairs guest room includes a large closet, while additional sleeping arrangements include a trundle bed in the living room.brbrbrbrFor easy planning here are the bedroom layoutsbrbrPrimary Suite With Ensuite Bathroom: 1 King Bed (second floor) brbrBedroom 2 With Ensuite Bathroom: 1 King Bed (second floor)brbrBedroom 3: 1 Queen Bed (a third bathroom is next to it)brbrLiving Room: Trundle Bed (2 twin beds)brbrbrbrThe kitchen is fully equipped with a refrigerator, electric range, microwave, sink, dishwasher, and ample counter space. Enjoy meals at the table in the dining room set for 6, with additional seating for 2 if needed. The deck features a dining table set for 6 and a bistro table. Large windows in the kitchen offer stunning views of the surrounding nature, and a Cuisinart coffee maker is available for your convenience.brbrbrbrThe living room is a peaceful haven with a large rug, and a square-shaped coffee table. It also includes a media console with a 70 Vizio TV outfitted with Apple TV and a Sonos bar, and a welcoming fireplace. brbrbrbrThere are TVs with Apple TV in every room, offering access to streaming services like Netflix, Disney+, and ESPN+. The Sonos sound system is installed throughout the house.brbrbrbrYou can enjoy the entire outdoor space, including the deck with dining and bistro table, as well as table and bench sets near the driveway. The property is surrounded by nature, providing opportunities to spot deer, owls and a variety of other wildlife right from the house. The home is conveniently located just a 2-minute drive or a 15-minute walk from town.brbrbrbrOther things to get excited about: brbr-The driveway accommodates up to 6 cars, you'll have ample parking. brbr-For your convenience, a washer and dryer is available brbr-Two steps lead to the front door and thirteen stairs with a landing in between lead to the upstairs bedrooms. brbr-Google Nest camera located above the garage. brbr-Hot water baseboard heat and cooled with Mini Splits A/Cbrbr-Decorative fireplace! brbr-Have a fun night in with amenities such as: a ping pong table, board games and yard games.brbrbrbrBook your stay today and immerse yourself in the serene surroundings and cozy atmosphere of our Great Barrington retreat.brbrbrbrWe look forward to welcoming you soon, standard rules like no smoking, no partying, no pets and being respectful of the neighbors apply.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.brbrbrbrThe Neighborhood:brbrGreat Barrington, nestled in the scenic Berkshires region of Massachusetts, is a charming small town known for its vibrant arts scene and stunning natural beauty. The town offers a variety of activities for outdoor enthusiasts, including hiking at Monument Mountain, which provides trails with breathtaking views of the Housatonic River Valley, and enjoying the serene waters of Lake Mansfield, perfect for swimming, picnicking, and boating. Beartown State Forest offers additional opportunities for hiking, mountain biking, and winter sports like snowshoeing and cross-country skiing.brbrbrbrCultural attractions abound in Great Barrington, with the Mahaiwe Performing Arts Center hosting a diverse range of performances, from concerts and theater productions to classic movie screenings. The Triplex Cinema is a beloved independent theater that showcases an eclectic mix of mainstream, indie, and foreign films. For those interested in history and literature, the W.E.B. Du Bois National Historic Site honors the life and legacy of the renowned civil rights activist and scholar, who was born in Great Barrington. Fans of folk music can visit The Guthrie Center, located in the Old Trinity Church, which serves as both a venue for community events and a tribute to Arlo Guthrie.brbrbrbrThe town's downtown area, particularly Railroad Street, is lined with unique shops, boutiques, and galleries, making it a delightful spot for shopping and exploring local art. The Berkshire Co-op Market, a community-owned grocery store, emphasizes local and organic products, reflecting the town’s commitment to sustainability and supporting local farmers.brbrbrbrGreat Barrington also boasts a diverse and vibrant dining scene. The Prairie Whale is renowned for its farm-to-table menu, offering hearty, rustic dishes made with locally sourced ingredients. Baba Louie's is a local favorite for its wood-fired pizzas, crafted with organic and locally sourced toppings. Gypsy Joynt provides a quirky and eclectic atmosphere with a menu that includes sandwiches, burgers, and a variety of vegan and vegetarian options. The Marketplace Café is a casual spot for breakfast and lunch, known for its fresh, locally made sandwiches, salads, and baked goods. For a taste of Mediterranean cuisine, Aegean Breeze offers an array of Greek dishes, including seafood and grilled meats. Number Ten is a standout steakhouse known for its high-quality cuts of meat and extensive wine list, while Bizalion's Fine Food offers a deli experience with gourmet sandwiches, soups, and salads, alongside specialty groceries like cheeses and charcuterie.brbrbrbrThe town hosts several annual events that draw both locals and visitors, such as the Great Barrington Arts Walk, which showcases local artists in galleries and shops throughout downtown, and the Berkshire International Film Festival, featuring a mix of independent and international films. The Holiday Stroll in December is a festive event with caroling, shopping, and family-friendly activities, adding to the town’s charm and sense of community. With its blend of outdoor activities, cultural experiences, and culinary delights, Great Barrington is a delightful destination for both residents and visitors.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon, standard rules like no smoking, no partying, no pets and being respectful of the neighbors apply. The fireplace is strictly decorative. For the comfort of all guests and to help us maintain the space, pets are not allowed on the property, even for short visits.brbrbrbrPlease note that the ping pong and foosball tables are located in the unheated garage. During the winter months, the garage may be too cold for use and storage of the patio furniture, limiting its suitability for gameplay.brbrbrbrDon't worry about accidental damage! Your rental includes an accidental reported damage waiver fee of up to $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 as the damage is reported to your host before you depart.
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Exceptional(38)

$516.73

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Private Vacation Home

An In-Town Beauty with Late Checkout

Great Barrington, Massachusetts, United States

The Berkshires and all its attractions are at your doorstep in this newly renovated, well-insulated 1900 Victorian, situated on a quiet residential street in downtown Great Barrington. A 5-minute stroll takes you to the heart of Main Street, while short drives take to you all the area's attractions: Butternut and Catamount ski centers, Tanglewood, the Appalachian Trail, Rockwell Museum, beautiful Lake Mansfield less than a mile away, and the multitude of mountain lakes in our region. brbrThe eclectic look and feel of my home reflects my twenty years as a boutique innkeeper and restaurateur in Bali, as well as being the daughter of a New York art dealer. You'll rest well on the comfy mattresses, 100% percale cotton bedding, duvets, and both down and microfiber pillows and enjoy fine Turkish cotton towels. I've stocked the kitchen with the high-quality cookware, equipment, and utensils (think vintage All-Clad, Lodge, Cuisinart, Vitamix, Nespresso, Microplane etc) that help produce a great meal. I also have my personal spice collection that I leave for guests to use. The spacious deck behind the house has a gas grill, dining table, comfortable chairs, and sun umbrella, suitable for 6-8 people. brbrWith the house's dimmable lighting throughout as well as decorative lamps and bedside reading lamps in every bedroom, you will feel the warm ambience of every space throughout the house. brbrAnd I never like having to check out at as early as 10 am, so please settle in and sleep in. Check out time is 2 pm. brbrbrbrbr
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Exceptional(6)

$785.87

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Private Vacation Home

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington, Massachusetts, United States

Evergreen Home Vacation Rentals invites you to this Great Barrington retreat, nestled on 4.7 park-like acres. This 3BR/3BA home is designed for wellness, featuring a private hot tub, a rejuvenating sauna, and a full gym.brbrEnjoy the convenience of a first-floor bedroom and den, plus two full baths on the main level. Located just 14 minutes from Butternut Ski Area and central to everything the Berkshires have to offer, this is the perfect base for relaxation and adventure. Book your stay!brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrbrThis private home is surrounded by beautiful hiking trails and central to many Berkshires activities.brbrGuests have access to all spaces within this home with the exception of a designated owner closet and utility room.brbrbrThis home is part of a large property, but is completely private and almost a football field away from the guest house. This is not a shared space.brbrThe open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided wood-burning fireplace, providing a cozy ambiance for your enjoyment. Delight in preparing your favorite meals at home with the convenience of our spacious kitchen island, offering ample room for culinary creativity. The open kitchen comfortably accommodates seating for four, with an additional kids' table for our younger guests to enjoy. The dining area in front of the fireplace comfortably seats 6 guests. brbrOn the ground level, you'll find one bedroom and two full bathrooms, offering both convenience and comfort. The first-floor bedroom is furnished with a Queen bed and a desk, perfect for those who need to work remotely. Both full bathrooms are conveniently located adjacent to the bedroom areas for added accessibility and ease. Additionally, there's a versatile den/office space that can easily convert into an extra bedroom with a queen-size pull-out sofa. brbrSunlight fills the hallway that connects the second floor. The second floor contains a spacious primary bedroom adorned with a Queen bed, alongside a charming second bedroom featuring two twin bunk beds. Completing this floor is a well-appointed full bathroom, offering comfort and convenience for all guests.brbrDescend into the finished basement, a haven for rejuvenation and activity. Unwind in the dry sauna, or make use of our fully-equipped gym, boasting a Peloton bike (bring your shoes!), bench, free weights, kettlebells, and all the essentials for your workout routine. Elevate your yoga practice with mats, blocks, and a full-length mirror, all while staying entertained with a motivating TV. For our younger guests, a dedicated children's play space awaits, brimming with an array of toys for endless fun and creativity.brbrStep into our serene park-like fenced backyard, where privacy and relaxation await you year-round in the inviting hot tub. Enjoy outdoor cooking with the convenience of a grill, and savor meals al fresco amidst the beauty of nature with our patio furniture and outdoor dining setup.brbrLong Pond is a reservoir in Great Barrington. It is a beautiful serene spot surrounded by nature. This is not a swimming/boating pond, but there is plenty of hiking all around the area. Pfeiffer Arboretum is just down the road which is a Land Conservancy on Long Pond featuring a .7 mile walking loop through diverse forest and wetland ecosystemsbrbrAlthough you will feel far from it all, downtown Great Barrington is just a quick 7 minute drive for shopping and restaurants! This home is only an 11 min drive to Lake Mansfield for swimming and beach access. Ski during the winter months with only a 14 minutes to Butternut Ski Area and 19 min Catamount Ski Mountain. Explore downtown Lenox and take a 20 minute drive to enjoy a show at Tanglewood.brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbr⭐️ LOCATION: This private home is surrounded by beautiful hiking trails and is central to many Berkshires activities, making it ideal for outdoor adventures and relaxing getaways.brbr⭐️ PETS: Small dogs may be allowed with prior owner approval. Please provide details about your pet before booking. A $100 pet fee applies if approved. No multiple pets allowed.brbr⭐️ PARKING: The property has a long circular driveway shared with the guest house, plus ample off-street parking for up to 4 cars.brbr⭐️ HOT TUB: Please keep the hot tub closed when not in use and ensure the jets are off before leaving. Guests use at their own risk and should be aware of potential health considerations.brbr⭐️ GUEST HOUSE: There is an additional guest house on the property that may or may not be occupied during your stay. The front parking circle is the only shared space. The home and backyard are fully private and fenced. The guest house cannot view the backyard.brbr⭐️ OCCUPANCY: The property can accommodate up to 8 guests. The first-floor den/office includes a pull-out queen sleeper sofa with an attached full bathroom. The sofa is a premium American Leather, more comfortable than standard pull-out couches.brbr⭐️ SECURITY: An exterior camera is located at the front door facing the driveway. There are no interior cameras.brbr⭐️ REGISTRATION: Town of Great Barrington Registration No: 003792brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.
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Bath 3

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