Vacation Home Rentals By Owner In Great Barrington, MA

$630.15

River Cottage: Riverfront Home, Walkable Community

Great Barrington, Massachusetts, United States

Summary:brbrWelcome to River Cottage, a beautifully renovated 3-bedroom, 2-bathroom riverfront gem in the heart of Great Barrington. Located along the scenic Housatonic River, this enchanting home offers the serenity of country living with the added benefit of being within walking distance to all the amenities of a vibrant, walkable community.brbrbrbrRiver Cottage is just a short stroll away from local favorites like Prairie Whale, charming shops, and the bustling Farmer's Market.brbrbrbrThe Space:brbrRiver Cottage boasts a pristine, completely renovated interior with gorgeous finishes throughout. The open-concept living and dining rooms flow effortlessly into a chef's kitchen, complete with a walk-in country pantry.brbrbrbrUpstairs, the primary bedroom features a king bed, complemented by two guest bedrooms—one with a queen bed and the other with another king bed. Two beautifully appointed bathrooms ensure privacy and convenience for all guests.brbrbrbrEnjoy your morning coffee on the charming, wrapping front porch or host a delightful al fresco dinner in the backyard’s outdoor dining area. The fenced backyard extends to the water's edge, offering stunning river views. Entertain guests on the back deck, relax in one of the many seating areas, or enjoy a cozy fire in the riverfront fire pit. brbrbrbrRiver Cottage is the epitome of a country escape, providing a perfect blend of tranquility and convenience. Whether you’re seeking a weekend getaway or a longer retreat, this idyllic home offers everything you need to relax, entertain, and enjoy the best of Great Barrington. Come experience the magic of River Cottage—where country living meets urban walkability in the most delightful way.brbrbrbrGuest Access:brbrGuests at River Cottage have access to the entire home, the front porch and yard, and backyard with patio, herb garden, fire pit, and river view.brbrbrbrThe Neighborhood:brbrRiver Cottage is located on a residential street in the heart of Great Barrington with walkable access to several grocery stores, outstanding restaurants, coffee shops, shopping, yoga, and more. You're also close to hiking, skiing, arts and cultural institutions. During warmer months the Great Barrington Farmer's Market operates every Saturday from 9am-1pm, providing the opportunity to cook family meals made with locally-sourced organic produce without getting in your car!brbrbrbrGuests at River Cottage have access to an easy walk into town via the pedestrian-only Cottage Street Bridge.brbrbrbrGetting Around:brbrRiver Cottage is approx 2.5 hours from Boston and just under 3 hours from New York City. You'll need a car to get here and get around the Berkshires, but downtown Great Barrington is just a short walk away! The house has moderate cell service, but the surrounding areas are full of cellular dead zones. We recommend downloading the region's online maps to your device prior to your arrival or any day tripping you do while you’re here.brbrbrbrOther Things to Note:brbrCooling: The home features window A/C units in both queen bedrooms, and mini-split units in the king bedroom and dining room.

3

Bed

2

Bath

6

Sleeps

$502.55

/ Nightly

Private Vacation Home

Chalet in Great Barrington near 2 Ski Areas

Great Barrington, Massachusetts, United States

Summary:brbrChalet Des Collines is a gorgeous country escape set on 2 pastoral acres of a lovely meadow in the Taconic Range. Enjoy skiing or snowboarding at Catamount (a 5-min drive) or Ski Butternut (a 10-min drive), mountain biking, hiking, cultural attractions or just relaxing in the comfortable Adirondack chairs by the fire pit in the meadow.brbrbrbrThe Space:brbrThis modern 4-bedroom, 2 bathroom chalet rests on 2 private acres within the Taconic Range, offering breathtaking meadow views and mere moments from skiing and mountain biking at Catamount!brbrbrbrInside, an abundance of natural light pours through expansive windows throughout the home. The stunning great room is warmed by a large fireplace and invites you to relax on a large sectional sofa – perfect for movie nights after a day on the slopes. Prepare gourmet meals in the fully-equipped kitchen and open the sliding doors to enjoy the beautiful outdoors. Dine al fresco on the beautifully manicured gardens, taking in the fresh mountain air.brbrbrbrUnwind after a day of adventure in one of the 4 beautifully appointed bedrooms. The primary suite upstairs offers a king bed and a large picture window framing the scenic meadow views. Bedroom 2 and 3 are on the ground floor and offer a queen bed or two twin beds. Upstairs, bedroom 4 boasts another large picture window and three twin beds, ideal for kids. Two spacious bathrooms both offer tub and shower combos.brbrbrbrHead downstairs to the basement recreation room for some friendly competition around the ping pong table. brbrbrbrVenture outdoors and embrace the tranquility of your surroundings sprawling over 2 private acres. Enjoy alfresco meals or lounging on the patio, fire up the grill for an evening barbecue under the stars, or simply relax by the fire pit and soak up the breathtaking scenery. brbrbrbrWe’ve thought of everything to make your stay as comfortable and enjoyable as possible. We have heating and mini splits for year-round climate control, SONOS speakers, and a large smart TV in the great room. Fresh linens, fluffy towels, and toiletries are all provided to make packing a breeze. Plus, there's a washer and dryer available for your convenience.brbrbrbrWith its perfect blend of modern design, amenities, and stunning natural surroundings, Chalet des Collines offers the perfect escape year-round, and mere moments from skiing and mountain biking at Catamount or Ski Butternut!brbrbrbrGuest Access:brbrWe provide electronic access to the house with a personal guest code. You'll receive the code 24 hours prior to checkin, though your code will only activate at check-in.brbrbrbrThe Neighborhood:brbrThe Berkshires are a stunning mountain region and Great Barrington is at the nexus of the Berkshires and the Hudson Valley, so gourmet grocers and large supermarkets are nearby, as well as outstanding restaurants, coffee and tea shops, shopping, yoga, and more. The perfect home base for hiking and camping at Mount Washington State Forest, the Chalet is also conveniently located for skiing, arts and cultural institutions, and more. You'll find plenty of things to do!brbrbrbrGetting Around:brbrChalet des Collines is 2.5 hours from Boston and just under 3 hours from New York City. You'll need a car to get here and get around and the drive will be beautiful! Since cell service can be inconsistent in the country, we recommend that you download the region's online maps to your phone before your trip.brbrbrbrOther Things to Note:brbrA/C: The home features mini-split units throughout, with one large unit in the living room and individual units in each bedroom on both the first and second floors.

4

Bed

2

Bath

8

Sleeps

$417.81

/ Nightly

Private Vacation Home

Light-Filled GB Oasis, Trails, Lake, Fireplace

Great Barrington, Massachusetts, United States

Summary:brbrModern forest hideaway in the Berkshires surrounded by trees, natural light, and quiet. Floor-to-ceiling windows, designer furniture, fireplace, and a fully equipped kitchen. Three comfortable bedrooms plus a large sectional for extra sleeping. Hiking trails nearby, Lake Garfield minutes away, and peaceful woodland views. A calm space to relax, read, cook, and reconnect with nature.brbrbrbrThe Space:brbrSlip away to a serene modern home tucked deep in the Berkshires forest, where floor-to-ceiling windows frame quiet woodlands and mornings start with birdsong. This thoughtfully curated home blends architecture, art, and nature for a calming reset. Designed and furnished by creatives, every detail is intentional, from the Dada chairs by Ferlea Italy to the Jean-Michel Frank dining table and design-forward book collection.brbrbrbrThe main level features an open living space with oak flooring, oversized windows, and a roomy sectional for movie nights or curling up with a book. A propane fireplace and Samsung smart TV logged into your favorite streaming apps, make it easy to settle in. The kitchen is equipped with high end Fisher & Paykel and Bosch appliances, a Bertazzoni range, induction cooktop, concrete tile, and a peaceful woodland view from the sink. Enjoy slow mornings with a single-cup coffee dripper and kettle.brbrbrbrThree bedrooms provide peaceful rest, each styled with warm textures and calming tones. The main-floor suite features a queen bed and its own ensuite bathroom, including a floating sink area and walk-in shower with handheld sprayer. Upstairs you’ll find a king bedroom with its own Smart TV, and a full bedroom perfect for kids or a solo sleeper. The second bath features a rain shower, handheld sprayer, and Toto washlet with heated seat. The large living room sectional can comfortably sleep two for extra flexibility. It’s a home designed for comfort and quiet, wrapped in forest stillness.brbrbrbrFor easy planning, here are the bedroom layouts:brbr • Bedroom 1: Queen Bed (main level, ensuite)brbr • Bedroom 2: King Bed (upstairs)brbr • Bedroom 3: Full Bed (upstairs)brbr • Living Room: Sectional that can sleep 2brbrbrbrOutside, you're surrounded by nature. The house feels like a modern glass terrarium in the trees, ideal for bird-watching, writing, meditating, or just breathing a little deeper. Hiking and running trails are close by, including nearby access to the Appalachian Trail. Lake Garfield is just minutes away for summer swims. A spin bike and small free-weight setup make it easy to stay active.brbrbrbrWhether you're relaxing by the fire, flipping through art books, or exploring favorites like Cantina 229, Prairie Whale, and Southfield Store, this escape gives you space to slow down, reset, and reconnect.brbrbrbrOther things to get excited about:brbr- Central Air to keep you cool all summer.brbr- Full size washer and dryer for your use.brbr- Parking on main landing space next to home can fit up to 5 cars.brbr-Approximately 3 steps to front door & main floor bedroom for those with limited mobilitybrbrbrbrPlease 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.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.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.brbrbrbrInteraction with Guests:brbrSupport team available 24 hours a day.

3

Bed

2

Bath

8

Sleeps

$635.98

/ Nightly

Private Vacation Home

Heated Pool & Hot Tub • Ideal Berkshires / Hudson Valley Getaway

Great Barrington, Massachusetts, United States

A stylish 4-bedroom farmhouse thoughtfully designed with modern comfort and historic charm. Located where the Berkshires meet Hudson Valley, the house is ideal for spring and early summer escapes.brbrSurrounded by mature trees, the house offers multiple spaces to gather, with a chef’s kitchen, outdoor dining, a hot tub, and a generous yard.brbrMinutes to Great Barrington’s dining, lakes, and hiking, and about 30 minutes to Tanglewood and Hudson — an ideal year-round escape for families or friends.brbrOur home is ideal for year-round visits. In the winter, it’s perfectly situated for skiing and cozy weekends by the fire. Summer is all about the pool, gardens, and long evenings outdoors. And throughout the year, you’ll enjoy beautiful grounds and easy access to the Berkshires’ cultural attractions, hiking trails, shops, and restaurants.brbrThe Berkshires are particularly lovely in the quieter shoulder seasons. Spring brings blooming landscapes and ideal hiking weather, while fall offers spectacular foliage and crisp, scenic afternoons. It’s also a wonderful time to work remotely from the Berkshires for a week or two — enjoying great restaurants, charming shops, and local culture without the summer crowds. The pace is relaxed, the scenery is stunning, and it’s the perfect balance of productivity and escape.brbrRooms & Indoor SpacesbrbrMain-floor brbrThe main living spaces flow seamlessly into one another — kitchen, dining room, living room, and family room — creating a layout that feels both connected and comfortably distinct. Generous windows throughout invite in natural light and surrounding greenery from every angle, bringing the outdoors in while preserving a sense of privacy and retreat.brbrThe lower level also includes a full bathroom, a small guest bedroom, and a convenient kitchenette or wet bar. A semi-enclosed porch extends the living space outdoors, offering a comfortable setting for al fresco dining in warmer months.brbrLiving RoombrThis warm and inviting living room features a classic stone fireplace and generous windows that bathe the space in natural light. An oversized L-shaped sectional offers ample room to gather or stretch out in comfort — ideal after a morning hike, a ski day at Catamount, an afternoon by the pool, or simply reading fireside.brbrTV / Family RoombrAdjacent to the living room, this additional gathering space gives guests a second option for relaxing—whether it’s movie night, quieter reading time, or a kid-friendly zone including some games and toys. brbrDining Room & Chef’s KitchenbrThe open-plan chef’s kitchen and dining area are ideal for shared meals and entertaining. The layout flows seamlessly into the living areas, making social time easy. The kitchen is modern and updated while preserving historic charm. brbrUpper Floor: brbrThe upper floor is anchored by a gracious landing that connects the three primary bedrooms. Two queen bedrooms offer charming reading nooks and separate dressing areas, creating intimate spaces within each room. The primary suite features an en-suite bath and opens onto a private terrace with Adirondack chairs overlooking the lawn and mature trees — an inviting spot for morning coffee or a quiet glass of wine at dusk.brbrPrimary Suite: On the second floor, the main bedroom includes its own full bathroom (with double sinks) a reading space, a Queen bed, plus access to a private deck. brbrTwo Additional Bedrooms: Also upstairs are two further guest bedrooms, one with a Queen bed, one with two Twin beds—ideal for family or friends.brbrAn Additional Full Bathroom & Laundry Area: A second full bath and a dedicated laundry space complete the upper level to make stays easy and comfortable for groups. brbrSummary of sleeping accommodations:brbr4 bedrooms total (1 ground-floor double bed + 3 upstairs, two Queen beds, two twin beds) brbr3 full bathrooms (1 on main level + 2 upstairs) brbrAdditional living spaces (TV/Family Room) providing flexibility for various guest groups.brbrOutdoor HighlightsbrbrHeated In-Ground Pool (Seasonal)brAcross the warmer months, guests can enjoy the heated pool—perfect for relaxing post-hike, or during summer get-aways. Pool is open from Memorial Day Weekend to Labor Day, sometimes later into September if weather allows. brbrHot Tub (Year-Round)brThe large hot tub is available all year long—so whether it’s snow-covered in winter or green and blooming in summer, guests can soak under the stars or crisp air. Like most outdoor tubs, temperature can vary slightly in very cold weather.brbrGrilling Patio & Outdoor Living AreabrAround the pool/hot tub area is a well-landscaped yard with a patio and grill—ideal for al-fresco dining, lounging, and gathering. A screened porch also offers a more protected outdoor dining spot when needed. brbrLocation & GroundsbrThe house sits on approximately 2.5 acres across from Catamount Ski Area and just minutes from Great Barrington and Butternut Ski Area—making it highly convenient for winter sports, yet private and peaceful.

4

Bed

3

Bath

6

Sleeps

$447.7

/ Nightly

Private Vacation Home

The Docent`s House - Honoring a Legacy

Great Barrington, Massachusetts, United States

Welcome to The Docent`s House, a home with a story worth staying for. For 18 years the woman who lived here walked visitors through the galleries of the Norman Rockwell Museum telling the stories behind the paintings. It`s a home built for gathering — families and friends all under one roof. Inside you`ll find a quiet tribute to the life of a Berkshire local: an educator, community activist, and longtime Rockwell docent whose legacy this home honors. Come for the Berkshires. Stay for the story.brbrBlack History Landmarks in The Berkshiresbr➥ W.E.B. Du Bois Boyhood Homesite - 15 minutes by carbr➥ Great Barrington River Walk - 10 minutes by car. A peaceful walking trail through downtown with interpretive markers honoring Du Bois and the town`s history.br➥ Clinton AME Zion Church - 10 minutes by car. Where a young Du Bois worshipped; now home to the Clinton Church Restoration, a center for African American heritage in the Berkshires.br➥ Ashley House (Sheffield) — about 25 minutes by car. The site where Elizabeth Freeman (Mum Bett) was enslaved and from which she launched the court case that ended slavery in Massachusetts.brbr✔ High-speed Wi-Fibr✔ Fully-equipped kitchenbr✔ Indoor fireplace (gas)br✔ Air conditioningbr✔ TVbr✔ Washer br✔ Dryerbr✔ Coffee & coffeemakerbr✔ Outdoor dining areabrbrOther notable Berkshire attractions w/ drive time . . . br➥ 3 mins to Ski Butternutbr➥ 8 mins to downtown Great Barringtonbr➥ 13 mins to Lake Garfieldbr➥ 16 mins Berkshire Botanical Gardenbr➥ 17 mins to Norman Rockwell Museumbr➥ 20 mins to Catamount ski areabr➥ 22 mins to TANGLEWOOD !br➥ 24 mins to Harlem Valley rail trailbrbr✦BEDS & BATHS✦brInside we have 4 bedrooms and 2 bathrooms, all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 Queen bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Queen bedbrBedroom 4 - 2 Single bedsbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a morning`s worth of coffee to get you startedbr - Learn more @ berkshire vacation rentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrNo pets of any kind allowed at this home. Emotional support animals are not allowed. By law service animals are allowed. If you are planning on bringing a service animal please reach out to us ahead of time so we can verify paperwork. If a pet is brought on the premises without alerting us the reservation will be cancelled.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrPrefer to communicate through the booking portal.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrPlease respect all quiet hoursbrPlease see the guest packet for more information.

Bed

Bath

Sleeps

$1077.75

/ Nightly

Private Vacation Home

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington, Massachusetts, United States

This charming former tavern and stage coach inn makes the perfect four season getaway. You'll feel like you've taken over your own private New England B&B. Enjoy everything the Berkshires has to offer from the shops and restaurants in Great Barrington, music and cultural events of Tanglewood to the north and great skiing at Butternut ski resort which is within walking distance of the house.brbrKnown locally as the Turning Point Inn, the main part of the house was built in 1850 and has a long history as a stage coach inn, local tavern and more recently a bed and breakfast. The layout is perfect for family gatherings when you want to be able to stay together but have your own private rooms to retreat to at night. It is conveniently located near many hiking trails (notably the Appalachian trail crosses nearby), waterfalls, swimming holes, parks, music festivals in the summer, and of course Butternut Ski resort just down the main road. Enjoy the great outdoors , downtown Great Barrington, or just a quiet night with good friends and family around the stove in a cozy dining room.brbrThis beautiful historic house features 7 fully furnished bedrooms and 6 bathrooms, 3 of which are ensuite. Each bedroom has it's own separate key and locking doors for added privacy. The main common spaces are spacious yet cozy, each possessing it's own unique charm. There is a family room with a wood burning stove and television with Chromcast and DVD player with a wide selection of DVDs. The sitting room has a working fireplace and maintains much of it's original character and decoration. The dinning room is cozy yet can comfortably accommodate 15 people with plenty of space to spare. As a former Bed and Breakfast the house is equipped with a commercial kitchen that includes a Viking stove and oven, coffee maker, toaster, water heater, microwave, dishwasher, large restaurant grade sink and professional cookware. We stock all the plates, bowls, cups and flatware you will need to entertain large groups. There is also a laundry room with a full size washer dryer.brbrDuring the summer months the main floor remains cool during the day with the stone and wood floors tempered by the cool evenings and mountain breezes. In the winter you can use the wood burning stove in the family room and the gas stove in the dining room. The fireplace in the sitting room is unfortunately under maintenance and not available for use at this time. The bedrooms on the second floor have their own air conditioners and individual smart heating controls to accommodate everyone's temperature preference. The house itself is nestled on 1 wooded acre with a large lawn. There is an outdoor picnic table where you can enjoy a glass of wine in the evening or your morning coffee. brbrPlease note that this is an old house built in the early 19th century. Things are worn and there are many imperfections. If you are looking for a brand new renovated experience, this may not be the house for you, but if you are looking for a clean large space with plenty of private bedrooms and bathrooms suitable for a large group of people and having a fun time then this is the place for you.brbrWe really fell in love with this house the moment we saw it and we know you will too. We look forward to hosting and sharing this special place with you!

Bed

Bath

Sleeps

$564.07

/ Nightly

Private Vacation Home

Berkshires / Great Barrington Chic & Cozy, Sleeps 10

Great Barrington, Massachusetts, United States

*20% month-long and 10% week-long discount automatically applied. If you don't see it applied, please feel free to reach out with questions. brbrOur home is the perfect location for your retreat to the Berkshires. Only minutes from downtown Great Barrington but you'll feel enveloped by nature in this comfortable and stylish home that sleeps up to ten guests, with no detail overlooked. brbrbrbrOriginally from 1886, but renovated as recently as 2024, this historic home with chic and thoughtful interiors has amazing nature views perfect for a country retreat in the Berkshires. This 2,400 sq foot Great Barrington home is beautiful all year around. It's located in the very best area of the fabulous Berkshires. Great Barrington is hip and charming (we have loads of recs!) and you'll feel like you're in the serene country while being less than 10 min from town. This cozy and chic home was featured in Domino Magazine!brbrbrbrNew mini-split A/C units installed in 2024 (white bedroom, green bedroom, yellow bedroom, living room, den/dining room). Kitchen and pink bedroom have powerful wall and window A/C units.brbrThe home is on 1.26 acres with protected wetlands all around and sleeps 10 people comfortably (4 queen beds + 1 king bed) and with lounging areas for hanging out including: a den with wood burning stove and piano, a dining room, a library nook, living room with a smart tv and sliding glass doors overlooking the protected wetlands. The eat-in kitchen features everything you need to cook for your crowd and seats 10 people. We stocked the kitchen with everything you need to take advantage of the BBQ, farmer's markets, specialty shops, and host a lovely dinner celebrating the bounty of the Berkshires. brbrThe home has been thoughtfully outfitted to make working remote from The Berkshires a comfortable possibility. There are three desks including a private dedicated office space. Cell service (which can be spotty elsewhere in the area) is very strong and reliable in this house and there is high speed WiFi with Google extensions for strong access throughout the home. brbrEnjoy the outdoors from the porch with a view of the back of Butternut Mountain (we're that close!) or sit in the backyard's picnic table on the gravel area and make s'mores around the fire pit. The perfect place for unbeatable star gazing on a clear night! brbrAll linens are hypoallergenic and anti-microbial. Bedroom floors are brand new cork, naturally antimicrobial and sustainably sourced. Kitchen is fully outfitted. We're happy to provide local restaurant and shopping recommendations.

Bed

Bath

Sleeps

$602.51

/ Nightly

Private Vacation Home

Jug End Crest | Fireplace • Sunroom • Central Air

Great Barrington, Massachusetts, United States

Welcome to your perfect getaway in the Berkshires! Nestled beside Jug End Reservation and the Appalachian Trail, this modern home boasts valley views and a cozy fireplace in the main living area. After a day of outdoor adventure, relax on the screened-in porch or enjoy the outdoor dining area, complete with a grill for meals outside with family and friends. Experience the unique charm of this one-of-a-kind retreat—your special escape awaits! Book now for an unforgettable experience!brbr✔ Picturesque backyard and valleybr✔ High-speed Wi-Fibr✔ TVbr✔ Firepitbr✔ Washer & dryerbr✔ Free parkingbr✔ Gourmet kitchenbr✔ Cozy fireplacebr✔ Pet-friendlybr✔ Pack n Play Travel Crib (Upon request)brbr ➥ 1 min to Jug End Reservebr➥ 5 mins to Catamount Ski Areabr➥ 6 mins to W.E.B. Du Bois National Historic Sitebr➥ 9 mins to Harlem Valley Rail Trailbr➥ 12 mins to The Mahaiwebr➥ 13 miins to Bish Bash Fallsbr➥ 17 mins to Ski Butternutbr➥ 19 mins to Bartholomew`s Cobble Reservationbr➥ 21 mins to Beartown State Forestbrbr✦BEDS & BATHS✦brInside we have 3 bedrooms and 2 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 King bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Twin bunk bedbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrThere is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

3

Bed

2

Bath

6

Sleeps

$800.86

/ Nightly

Private Vacation Home

Pothul Perch | Walk to Lake • sleeps 8

Great Barrington, Massachusetts, United States

Charming four bedroom house on the hill with convenient access to downtown Great Barrington. Just a few blocks to the beach at Lake Mansfield!brbrA ten minute walk puts you right into the middle of downtown Great Barrington, full of coffee shops, boutique shops, and charming little restaurants. brbrIf town isn`t your thing, swing by one of the organic grocery stores and cook you and your guests a meal to enjoy on the back patio.brbrPerfect getaway for families escaping for the weekend!brbr✔ Garagebr✔ High-speed Wi-Fibr✔ Smart TVbr✔ Full kitchenbr✔ Washer & dryerbr✔ Free parkingbr✔ Heatingbr✔ Outdoor dining areabr✔ Gas Grill & Outdoor fireplacebr✔ Pack n Play Travel Crib (Upon request)brbr➥ 5 mins to The Mahaiwebr➥ 6 mins to W.E.B. Du Bois National Historic Sitebr➥ 10 mins to Ski Butternutbr➥ 14 mins to Beartown State Forestbr➥ 15 mins to Catamount Ski Areabr➥ 17 mins to Norman Rockwell Museumbr➥ 19 mins to Harlem Valley rail trailbr➥ 22 mins to Lake Garfieldbr➥ 25 mins to Bish Bash Fallsbrbr✦BEDS & BATHS✦brInside we have 4 bedrooms and 2.5 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 King bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Queen bedbrBedroom 4 - 1 Full bedbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrNo pets of any kind allowed at this home. Emotional support animals are not allowed. By law service animals are allowed. If you are planning on bringing a service animal please reach out to us ahead of time so we can verify paperwork. If a pet is brought on the premises without alerting us the reservation will be cancelled.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrOne parking space in the garage available for guests. Additional parking in driveway.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

Bed

Bath

Sleeps

$1109.18

/ Nightly

Private Vacation Home

Summer Chalet w/ Pool, Firepit + Private Hiking Trails in Great Barrington

Great Barrington, Massachusetts, United States

Nestled in the foothills of East Mountain, just minutes from the center of Great Barrington, this woodsy summer chalet has been completely reimagined with featuring stunning 30-foot ceilings with skylights, an open floor plan, a wood-burning fireplace, a chef's kitchen with an automated downdraft venting system, new patios, decks, balconies, a refinished seasonal swimming pool, gas & charcoal grills, private hiking trails abetting the State Forest, and an abundance of unique outdoor areas to enjoy summer in the Berkshires. brbrEach bedroom is equipped with an individual climate control unit. The Primary Suite features a private balcony overlooking the pool, a large walk-in shower and a separate soaking tub with jacuzzi jets. The East bedroom often doubles as an office, equipped with a desk and a printer. It also boasts of an enormous private patio to watch the stars or do yoga surrounded by trees. The Middle bedroom is perfect for kids or an adult couple and has its own closet space. The West bedroom features a small porch with direct access to the yard and two twin-sized beds. The living room features a 70 SmartTV w/ a bluetooth enabled soundbar, to stream all of your favorite music, podcasts, shows, movies and live events.brbr***PLEASE NOTE*** There is a bridge closure that does add time coming in and out of Great Barrington town center. brbr*** ALSO *** We recently added blinds/shades and curtains to all of the windows in the upstairs bedrooms (not pictured in the photos)

Bed

Bath

Sleeps

$411.06

/ Nightly

Private Vacation Home

Cozy Great Barrington Home ~ 1 Mi to Ski Resort!

Great Barrington, Massachusetts, United States

Art and history meet breezy mountain adventures at this Great Barrington vacation rental! This 4-bedroom, 2-bathroom house boasts a private setting, the comforts of home, and an ideal location 1.3 miles from Butternut Basin Ski Lodge. See the sights at the Norman Rockwell Museum, attend a summer concert at Tanglewood, or stop by the Naumkeag, a 48-acre masterpiece known for its elegant public gardens and historic home - all within 15 miles so you can make the most of your stay in the Berkshires.brbr-- THE PROPERTY --brbr1,650 Sq Ft | Dutch Colonial | Completely Remodeled | Outdoor Gazebo w/ Gas Grill (seasonal)brbrModern updates and comfortable accommodations make this exquisitely located home the ideal spot for your weekend getaway with friends!brbrMain Bedroom: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds | Living Room: Full Rollaway BedbrbrINDOOR LIVING: 40-inch wall-mounted & gaming quality Smart TVs (in each bedroom), 65-inch living room Smart TV, open layout, hardwood floorsbrKITCHEN: Fully equipped, stainless steel appliances, Keurig drip coffee maker, toaster oven, cooking basics, dining table & chairsbrGENERAL: Free high-speed WiFi (400 Mbps), washer/dryer, linens & towels, electric baseboard heaters, electric blow dryer in each bathroom, electric split mini heaters for each room (heat & A/C)brFAQ: Stairs to access, all bedrooms on 2nd floor, complimentary starter set (bottled water, coffee, tea, & laundry detergent), 4 exterior security cameras (facing out)brPARKING: Driveway (4 vehicles)brbr-- THE LOCATION --brbrSKIING: Butternut Ski Area (1.3 miles), Catamount Mountain Resort (13.7 miles), Bousquet Ski Area (18.9 miles), Jiminy Peak Mountain Resort (35.7 miles)brOUTDOOR ADVENTURE: East Mountain State Forest (0.9 miles), Monument Mountain (6.0 miles)brARTS & HISTORY: Naumkeag (9.4 miles), Norman Rockwell Museum (9.8 miles), Berkshire Botanical Garden (10.2 miles), Tanglewood (13.2 miles), Berkshire Museum (21.2 miles), Hancock Shaker Village (21.5 miles)brLOCAL EATS: Xicohtencatl Restaurant (3.4 miles), Aegean Breeze Restaurant (4.0 miles), Baba Louie's Sourdough Pizza (4.4 miles), The Bistro Box (6.0 miles)brAIRPORTS: Bradley International Airport (45.1 miles), Albany International Airport (57.9 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: The property requires stairs and may be difficult for guests with limited mobility br- NOTE: All bedrooms are located on the 2nd floor br- NOTE: The property sleeps 8 guests in the 4 beds, but the maximum occupancy is flexible up to 9 with the use of the full rollaway bedbr- NOTE: Your safety matters. This property features 4 exterior security cameras. Camera 1 is located by the front door facing the front outdoor entry, camera 2 is on the garage facing the driveway, camera 3 is on the side of the house facing the driveway, and camera 4 is on the back of the house facing the back sliding glass door entry. All cameras are outward facing and do not look into any interior spaces. The cameras record video when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detectedbr- Masstaxconnect # 1-000-963-648br- MassConnect Room Occupancy Certificate #: C0298621130

4

Bed

2

Bath

9

Sleeps

$1288.69

/ Nightly

Private Vacation Home

Renovated family friendly house close to everything and endless views

Great Barrington, Massachusetts, United States

Bright, comfortable house with pool and comfortable outdoor seating and eating areas, endless mountain views in front and acres of open pasture in back. Four bedrooms and 3.5 baths. Two bedrooms with king sized beds, large closets and en suite newly renovated bathrooms. One bedroom with queen sized bed and twin bed. One bedroom with twin bed and bunkbed. Reading room can serve as extra bedroom. Remodeled, fully stocked kitchen.brbrbrWood burning fire placebrTelevision, cable and internetbrWasher/dryer on ground floorbrTwo car garagebrFully stocked kitchen with 12 place settingsbrPing pong table brChildren's outdoor swingset and slidebrHeated swimming pool with outdoor lounge furniturebrOutdoor shower brOutdoor table with large umbrella brOutdoor fire pit (marshmellows!) with seating brbr3 miles to center of Great Barringtonbr4 miles to Guidos and Big Ybr7 miles to Butternut br7 miles to Catamountbr4 miles to Egermont Country Club (public 18 hole golf course)br12 miles to Tanglewoodbr120 miles from Manhattanbr140 miles from Boston

4

Bed

3

Bath

10

Sleeps

$465.79

/ Nightly

Private Vacation Home

Private Home in the Berkshires with Hot Tub

Great Barrington, Massachusetts, United States

Welcome to your private country escape — a newly renovated 2-bedroom, 1-bath home surrounded by 2 acres of open lawn and 5 acres of wooded area and natural beauty. Tucked away on a quiet road, this serene retreat offers the perfect blend of modern comfort, rustic charm, and total relaxation. Inside, the open-concept design creates a bright and airy feel, with large windows that bring the outdoors in. The fully equipped kitchen flows seamlessly into the cozy living space, making it easy to cook, unwind, and connect. Every detail has been thoughtfully updated — from the stylish finishes and new flooring to the warm, inviting décor that makes you feel right at home. Step outside to your private deck and sink into the bubbling hot tub as you take in the peaceful countryside views. With no city noise or close neighbors, you’ll have all the privacy you need to truly unwind — perfect for sipping wine under the stars or enjoying your morning coffee as the sun rise. Whether you’re looking for a romantic weekend, a family getaway, or a quiet place to recharge, this home is a hidden gem. Explore local trails, lakes, and small-town shops nearby, then return to your private haven where comfort, calm, and wide-open space await.

Bed

Bath

Sleeps

$590.87

/ Nightly

Private Vacation Home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Lovely 4 bedroom, sleeps 10. 3-story classic Victorian home in family-friendly neighborhood. Clean modern interiors and nature-enjoying exteriors including gardens, covered porch, screened deck and fenced yard. Easy walk to Main Street and Lake Mansfield. brbrLike winter sports This home is a great ski season rental as it's a quick 9 minute drive to Butternut Ski Area and Tubing Center and only 14 minutes to Catamount Mountain Resort. brbrBuilt in 1903, this updated and yet stunning example of Victorian craftsmanship is a perfect place for family and friends looking to find an easy getaway in the Berkshires. The interior is sunny, bright and modern with charming Victorian details throughout. brbrThe house is well appointed on the ground floor level with a large living room, music parlor including a grand piano and large assortment of art and design books, large eat-in kitchen, separate dining room area with large farm table and French café chairs with seating for 8, ½ bath, and large pantry/laundry room with side by side front loading washer and dryer. The living room and parlor comfortably seats 10 guests. brbrThere are inviting touches throughout the house such as: lovely artwork, books, games, puzzles and toys to entertain both children and adults! The kitchen is well equipped with high-end stainless appliances and All-Clad and Le Creuset cookware. All tools needed for baking are available including a Kitchen-aid stand mixer. Kitchen includes a large assortment of high-end small appliances including microwave, food processor, blender, coffee maker and 4-slot toaster. At the kitchen sink, a Multi-Pure water filter system is built-in. The deck and screened porch are accessed from both the kitchen and the living room.brbrThe second floor has 2 bedrooms: the primary suite with a king bed and full bathroom with tub/shower combination, en suite. The second large bedroom has a queen bed and access to the 2nd floor porch. There is a second full bathroom on this floor with a walk-in shower.brbrThe third floor is a delightful converted loft-like attic space with two rooms. One bedroom has 4 twin beds: 2 extra long singles and the third is a twin trundle, which can be made up as a twin, two twins or a king - perfect for a group sleepover or family! The other room, best for children, has one extra-long twin and small trundle bed. All three floors have central air-conditioning and heating. The extra-long twins have organic rubber mattresses. Due to their generous length and quality, these mattresses are very comfortable for adults as well as children.brbrOutside you have a delightful front sitting porch and lovely cottage gardens with pathways leading to the front walk and side parking area. The back sun deck is private, with outdoor seating and a grill for dining al fresco. There is also a cozy screen tea porch on the side of the house, accessed through the family room. The yard is fenced with a delightful playhouse!brbrLocated in the sought after neighborhood called “The Hill”, this home is an easy 5-minute walk to the center of downtown Great Barrington for a meal, shopping, shows, cinema, galleries and much more. This home is also an easy walk (or 3 minute drive) to Lake Mansfield Park for swimming. (There is a sandy beach, children's playground equipment and a lifeguard on duty!) You can enjoy picnicking and having fun on the climber & swing sets. No motorboats allowed but canoes/kayaks are available for rent in town or bring your own! brbrFor music lovers, it's a 25 minute drive to Tanglewood, and for dance enthusiasts it's a 25 minute drive to Jacob’s Pillow.brbrAmenities:brArrival Day FlexiblebrChildren WelcomebrPets ConsideredbrSmoking Not AllowedbrDecked areabrCentral heatingbrAir ConditioningbrTelevisionbrGamesbrToysbrSmart TVbrBooksbrLaptop FriendlybrKitchenbrRefrigeratorbrMicrowavebrCoffee MakerbrDishwasherbrDishes UtensilsbrSpicesbrStovebrHighchairbrToasterbrOvenbrBBQbrFridgebrFreezerbrHeatingbrCarbon Monoxide DetectorbrGrillbrDeck Patio UncoveredbrGardenbrPrivate yardbrBalcony/TerracebrHouse Cleaning OptionalbrWifibrFishing FreshwaterbrHikingbrSkiingbrSnowboardingbrGolf course within 30 min drivebrFamilybrDowntownbrTownbrLive TheaterbrEco TourismbrBathtubbrHigh ChairbrChildren's Books and ToysbrTable Corner GuardsbrPack n Play Travel CribbrRoom Darkening ShadesbrChildren's DinnerwarebrStair Gates

Bed

Bath

Sleeps

$1507.95

/ Nightly

Private Vacation Home

Stunning Renovated Victorian

Great Barrington, Massachusetts, United States

Located in the beautiful Berkshires, MA, the 5000 sqf home is located in a desired neighborhood known as the Hill.” The sun filled house is on a quiet no outlet road and sits on 2.5 acres of landscaping including blueberry bushes, maple tree, lawns, mature flowers, and custom cobblestone. In spite of being only a 15 min walk from downtown, it feels very away from it all with trees in every window and privacy.brbrConnections to the Appalachian trail within 10 minutes. Lake Mansfield is a 15 min walk. The Green River, with a swimming hole, is a 15 min hike through the woods. The Mahaiwe, a movie theater and the great thriving restaurants, boutiques, toy stores and coffee shops of downtown are a 15 minute walk. Tanglewood is a 20 minute drive. Butternut is a 10 minute drive.brbrThe historic home was built in 1905 and was one of the first in Great Barrington to receive electricity. It has been lovingly renovated and restored from the ground up. Many original details were restored to new condition (windows, radiators and the like) and modern conveniences added. There is central air conditioning, whole home audio system, movie room w/ mounted 65 inch 4k television, surround sound, double pane windows, heated floors in the bathrooms and kitchen. There is a second 4k television in the den for when the kids don't want to watch the same movie as the adults - also with high end surround sound. Sony Playstation and multiple streaming devices all updated to 4K technology. The gourmet cook's kitchen includes a large granite prep area, 2 deep sinks, Wolf Stove, large SubZero, and 2 Bosch dishwashers for easy clean up. brbrThe house is oversized but still cozy with brand new sheets from Brooklinen, new towels, lots of blankets, and well designed locally bought furniture and rugs. There are games and a library of classics and NYTimes bestsellers for ages 2 - adult. In keeping with the classic feel, there is a high end record player in the library for afternoons playing chess and cards. Two large wood burning fireplaces make it homey during the winter.brbrEnjoy the fresh summer air on the large screened in porch, play ping pong, or enjoy a meal in the fresh air on the screened porch dining table. Ample lawns and private outdoor space, especially for an in town property. Weber Grill on large stone patio for for preparing summer meals, nine person sunken hot tub on mahogany deck and a wood swing set and slide set up for the kids. brbrNursery was painted and set-up in 2022 and has toddler toys available for use. Farrow and Ball paint and natural fiber rugs used throughout most of the house. Fragrant free and organic or non-toxic cleaners used. Plates and serving ware for 12 from Crate and Barrel, new in Fall 2024.brbrAlso available for seasonal or year-long rental.

Bed

Bath

Sleeps

$577.12

/ Nightly

Private Vacation Home

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington, Massachusetts, United States

**WINTER** Hit the slopes in minutes. Less than 10 minutes to Ski Butternut and less than 15 minutes to Catamount Ski Mountain**Adventure Awaits in Every Season. Hike. Ski. Swim. Relax. Repeat****brCombining the beauty and solitude of our 5+ acres of wooded hills, all the while sitting conveniently just 0.7 miles from the magnificent town of Great Barrington. Sleeps 10 | Wi-fi | 2 Zone AC and Heating| Private Outdoor HOT TUB.brbr---THE PROPERTY---brNestled by trees and tucked at the end of a long private driveway. Tons of yard space provide fresh views while sitting on the large front porch or sipping your favorite drink in the ultra-comfortable screened in back porch. Cap off the night sharing stories and making memories by the outdoor firepit. Warm up after a long day slope side in the brand new Outdoor Hot Tubbrbr**Easy One Level Living in this Simple & Modern Ranch with Outdoor Hot Tub***br**Complimentary Spectrum Cable + Wi-Fi + Smart TV | 2 zone AC and Heating system**brbrAll Bed Linens and Bathroom Linens are providedbrbrBedroom 1: King Bed + Large Sofa and Walk in Closet + DresserbrbrBedroom 2: King Bed + Closet + DresserbrbrBedroom 3: Two Double Beds + Closet + DresserbrbrLiving Room: 1 Pull out Queen SofabrbrBathroom 1: Master Bathroom with double sinks, closet, and Large ShowerbrbrBathroom 2: Large Bathroom with Bathtub & ShowerbrbrKitchen: Dine in or Entertain with your friends in this open concept Kitchen. Quartz Countertops, Stainless Steel Appliances, Toaster, Coffee Maker, Dishwasher, Dishes, Glasses, Pots, Pans, Serving Platters, Cooking utensils, + plenty of silverware. 2 Counter Stools + Dining Table seats 6brbrLiving Room: Offers plenty of seating with the overly large sectional sofa. Pick a spot to unwind after a day of exploring. Smart TV + Spectrum Cable + DVD Player + Wi-fibrbrOutdoor Amenities: Large Front Porch | Screened in Porch | Outdoor Grill and Dining Area | Lawn Games in Deck Box | Fire Pit| Outdoor Hot Tubbrbr**Dogs are on a case by case discretion and needs the Owners approval. $50 per Dog FeebrbrParking for 3-6 VehiclesbrbrWasher | Dryer | Iron available brbr**Complimentary Pack n Play with Mattress + Portable Booster Seat available**brbr---THE LOCATION---brSitting on nearly 6 acres, enjoy the sights as you may encounter wildlife such as bugs, birds, bears, bobcats, and deer just to name a few.brLess than 1 mile to downtown Great Barrington & Lake Mansfield. br--- POLICIES----br- Property Registration Number C043443113Ebr- No Smokingbr- Onsite parties or group events are strictly prohibitedbr- Notice that no excessive noise shall occur after 8:00 PM or earlier than 8:00 AMbr- Must be at least 25 years old to bookbr- Government-issued photo identification and credit card, debit card, or cash deposit may be required at check-in for incidental charges.br- Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteedbr- NOTE: This unit has exterior-facing cameras. They do not look into interior spaces within the propertybrSAFETY FEATURES: Fire Extinguisher | Smoke Detector | First Aid Kitbr-----LOCAL ATTRACTIONS----brGreat Barrington, Lenox, Stockbridge, Lee, Tanglewood, & Pittsfield. Fun in any season. Take your pick. The abundance of lakes, mountains, and woods provides a variety of outdoor activities from trail hiking, biking, fishing, ziplining, kayaking, Skiing, Snowboarding, snowshoeing, festivals, music concerts, apple and berry picking, farmers markets, and theatrical performances. Fill up with the famous Berkshire food scene showcasing a variety of cultural and culinary experiences. Want more Explore the infamous New England architecture, homes, and historical sites. Chill out to some local and some famous performers. The experiences are unlike anywhere else. The

Bed

Bath

Sleeps

$569.67

/ Nightly

Private Vacation Home

Outdoor Sauna, Hot tub, Fire Pit, Dogs Welcome!

Great Barrington, Massachusetts, United States

Relax with the whole family or escape with your partner for a romantic getaway to Lovers Lane. Surrounded by trees and set against the backdrop of Monument Mountain, you'll have everything you need in this quiet, private setting to fully enjoy some time away.brbrSoak in the hot tub and relax in the outdoor sauna while taking in the beautiful view of Monument Mountain.brbrIt's a short drive to downtown Great Barrington & Stockbridge where you will find cute shops & great dining. Go skiing at Butternut, see live music at Tanglewood or hike Monument Mountain. Good times await at Lovers Lane in the Berkshires.brbrThis house was built in 2022 and everything is brand new. The original building was a tannery that made and fit the saddles for the Budweiser Clydesdales. Open floor plan living so plenty of room for the whole family to gather for a meal or in front of the TV for movie night. There is plenty of space to get away for some alone time to nap in one of the bedrooms or take a nature walk in the woods on the property. The house sits back from the street down a private driveway nestled in the trees.brbrWe are right next door to the Little Lion Motel so if you are traveling with extended family and have a big group that needs additional lodging, book them there! It's just a short walk across the backyard from our house.

3

Bed

2

Bath

6

Sleeps

$291.21

/ Nightly

Private Vacation Home

Great Barrington Farmhouse near Lake Mansfield

Great Barrington, Massachusetts, United States

72 CHill Road is a cozy 1860’s farm house with mid-century modern flair. A 7-minute drive to downtown or Butternut, this calm Berkshire refuge is the perfect place for a country vacation with all the amenities of town life. The house has 3 bedrooms, living room, fully equipped kitchen, dining room and sun porch. Out back you will find expansive views, mature trees and close to an acre of lawn with spaces to lounge, practice yoga under the willow or relax in the hammock overlooking East Mountain.

Bed

Bath

Sleeps

$1386.64

/ Nightly

Private Vacation Home

Berkshires Estate w/ Heated Pool by Evergreen Home

Great Barrington, Massachusetts, United States

Evergreen Home Vacation Rentals invites you to your private 60-acre Berkshires paradise. Ideally located 10 minutes from Great Barrington and Stockbridge, this estate features private trails, a heated saltwater pool, and a pool house with a kitchenette.brbrWith stunning views and ample space, this retreat is perfect for large groups. Enjoy easy access to Tanglewood and Jacob’s Pillow, or simply unwind in your own secluded sanctuary. Experience the ultimate Berkshire escape—book your stay today!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.brbrbrThe home is set far off a main road in Great Barrington, the setting is rural and you cannot see the neighbors or see / hear any car traffic.brbrGuests will have private access to the home, and property during their stay.brbrThis is an established 5-star rental property —check the photos to see the glowing reviews!brbrThe open concept main floor of the house features a fully stocked chefs kitchen with a large island, high ceilings, and everything you could need for meals at home. The kitchen also includes a large dining table that can seat up to 8 guests. Cozy up in the family room located off the kitchen and enjoy the view of the property through the large windows.brbrDown the hall, the spacious living room provides the perfect space to enjoy a movie or play a board game with the whole family. Large windows throughout the room allow for natural light to pour into the living area. Attached to this room is the sun porch which contains additional seating and dining areas as well as a small book collection. brbr3 of the 5 spacious bedrooms are located on the first level of the home. The primary bedroom features a king bed, sunlit seating area, and ensuite bathroom. The other two bedrooms on the first floor also contain king sized beds and both have a pullout couch to accommodate different sleeping arrangements. There are two half baths and one full bath with a walk in shower located on the first floor.brbrThe second floor of the home contains the other two bedrooms, one with a king bed and the other with a queen bed. There is a full bathroom with a tub/shower combo upstairs.brbrThe lower level of the house includes the washer and dryer units, pool table, and workout equipment. brbrStart your morning on the front deck, sipping coffee and taking in the sounds of nature. Spend the day on the back deck lounging in the sun or under the awning while enjoying the views of the property. brbrCool off in the salt water pool and keep your food and beverages in the detached pool house equipped with a sink, dishwasher, refrigerator and bathroom. There is also an outdoor shower to rinse off post pool. Explore the private trails maintained around the property.brbrSpend the evening grilling and sitting around the fire pit on the back patio, head into town to one of the many restaurants or bars, or hire an incredible private chef to come in for a gourmet meal. The options are unlimited!brbrLocated 10 min from downtown Great Barrington or Stockbridge, 5 min from Butternut Basin, and 20 min from Tanglewood and Jacob's pillow.brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbr⭐️ LOCATION: This home is set far off a main road in Great Barrington, offering a peaceful, rural setting with no visible neighbors or traffic noise.brbr⭐️ PETS: No pets allowed.brbr⭐️ PARKING: Free on-site parking is available.brbr⭐️ POOL: Open seasonally May through October, with exact dates determined by weather.br• June 1–Labor Day: Heated to 82°F at no additional cost. Guests may request a higher temperature for an extra fee—please contact us in advance.br• May & after Labor Day: Pool heating may be available for $150/day, but is not guaranteed. Advance notice required to ensure readiness.br• Heating above 82°F during June–Labor Day is available for an additional fee; please contact us prior to arrival.brbr⭐️ WORKOUT EQUIPMENT: Guests may enjoy a Peloton (bring your shoes!), TRX, and resistance bands during their stay.brbr⭐️ COMMERCIAL USE: Owners may allow commercial photography or filming with prior permission. Additional fees may apply—please inquire before booking.brbr⭐️ 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.

Bed

Bath

Sleeps

$774.25

/ Nightly

Private Vacation Home

Jaw dropping mountain & lake views in this stylish mountain home….

Great Barrington, Massachusetts, United States

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. brbrPrivate mountain top adventure awaits.. brbrCentrally located in Southern Berkshire County: 10 minutes from Butternut ski, 15 minutes to Great Barrington, 20 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.brbrGreat Room: Spacious open floor plan great for entertaining friends and family. Living room is furnished with 2 comfortable deep seated sofas, accent chair and 2 ottomans and 2 large coffee table’s, Relax and enjoy collection of movies on dvd players, listen to music on the stereo system or play games (we have a variety of board and card games).brbrFamily room (downstairs) with large sectional and daybed for extra sleeping. There is a TV and dvd player. brbrChef’s Kitchen: Stainless steel appliances, large island that seats 6 and dining table that seats six...brbr4 Bedrooms: 1 King size, 3 queen size all with luxury mattresses and bedding.brbr2 Bathrooms: Master bathroom (upstairs) features with shower and deep soaking tub.br*we are building an additional 3rd bathroom off the hallway, but for now the bathroom upstairs is in the master bedroom that is shared with the guest bedroom.brbrScreened sunroom nestled amongst the woods with beautiful views of the lake… Provides a comfortable setting to relax and includes a sectional sofa, chair & ottoman and table with 4 chairs to enjoy the outdoors.brHammock’s, fire pit, hot tub and grill set up weather permitting… brbrNOTE: brDriveway: The house is located on the top of a long private gravel road, it gets snow plowed when the snow reaches 4” but it’s best to have a car that suitable in the snow. brbr We have updated home to include Central Heat & Air Conditioning Fall 2019.brbrInternet: Wifi throughout the home.brbrMovies & Cable TV:br2 Large Flat Screen TV’s equipped with Smart TV's and DVD players including premium’s like Netflix, HBO, SHOWTIME and STARS. brbrStereo system with speakers is set up in the great room with record player and aux cord to hook your phone to play any music on your phone library. brbrPhone:brThere is also no house phone some cell phone providers work better than others. brbrWe will be providing all our guests with our How to's, House Rules and an inventory list that each guest must read and email back with confirmation that they have read and understand.brbr* ID verification required before booking.

4

Bed

2

Bath

9

Sleeps

Vacation Home Rentals By Owner In Great Barrington, MA

$630.15

$502.55

$417.81

$635.98

$447.7

$1077.75

$564.07

$602.51

$800.86

$1109.18

$411.06

$1288.69

$465.79

$590.87

$1507.95

$577.12

$569.67

$291.21

$1386.64

$774.25

Rent a place that suits your needs

Most popular vacation rentals in Great Barrington

$1325.32

$1386.64

$1414.90

$1507.95

$1638.27

$1647.89

$2047.83

$3773.86

$11193.94

$411.06

Most Popular Cities in Massachusetts