Vacation Home Rentals By Owner In Great Barrington, MA

Showing 75 Of 75 Vacation Rentals

$414.13

Twin Maple Farm: Charming Modern Farmhouse

Great Barrington, Massachusetts, United States

This updated 1920s farmhouse centrally located in the Berkshires is great for family vacations with a large backyard for kids to play and parents to relax. The large living and dinning rooms allow for family time but bedrooms provide privacy. Down the street is Taft Farms, great for fresh fruits, vegetables and baked goods. Downtown Great Barrington (5 min. drive) is a fun area for shopping and food. Within a 20 minute radius there are ski areas, hiking trails, waterfalls, museums, and theaters.brbrThe Neighborhood: The greatest advantage about the neighborhood surrounding Twin Maple Farm are all of the local food options only minutes away. Just a quarter of the mile down the road you will find Taft Farms, great for fresh fruits, vegetables and baked goods. Depending on the season, Taft Farms also has a petting zoo, corn mazes, and much more. A mile past Taft Farms is Berkshire Mountain Bakery, some of the best bread you will ever try! Not only do they have great bread, they also have amazing Take 'N' Bake pizza. Adventure a little further down the street and you will find Windy Hill Farm great for pick your own berries and apples, Butternut Ski Area, and downtown Great Barrington.brbrInteraction with Guests: My intention is that every guests fully enjoys Twin Maple Farm and their time in the Berkshires. I offer assistance as needed but also respect guests' privacy. Upon arrival I meet guests to show them around and answer any questions such as good places to eat, the best things to do with kids during each season, etc. Once guests are settled in I respect their privacy but am only a phone call away.

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Sleeps

Exceptional(3)

$831.45

/ Nightly

Private Vacation Home

The Summerwood Hideout | Mins to Downtown! • Pool

Great Barrington, Massachusetts, United States

Book your getaway today to Long Pond Luxe in the Berkshires! This recently renovated home features a 3bd / 3 bath main house and a charming pool house for the inlaws or the teenagers that want their own space. Relax by the pool tucked into the full patio, perfect for entertaining in a private woodsy setting just outside Downtown Great Barrington. Whether it`s outdoor adventures or relaxing getaways, this peaceful spot has everything you could ask for in a fun, memorable Berkshires escape!brbr✔ Poolbr✔ Poolhouse (only included in the booking from Memorial Day Weekend through Columbus Day Weekend)br✔ High-speed Wi-Fibr✔ Smart TVbr✔ Fully equipped kitchenbr✔ Washer & dryerbr✔ Fireplacebr✔ Outdoor firepit & Gas Grillbr✔ Pet-friendlybr✔ Pack n Play Travel Crib (Upon request)brbr➥ 8 mins to The Mahaiwebr➥ 9 mins to W.E.B. Du Bois National Historic Sitebr➥ 11 mins to Ski Butternutbr➥ 12 mins to The Lion`s Denbr➥ 13 mins to Chesterwoodbr➥ 14 mins to Norman Rockwell Museumbr➥ 14 mins to The Unicorn Theatre: Berkshire Theatre Groupbr➥ 14 mins to Beartown State Forestbr➥ 14 mins to Berkshire Botanical Gardenbr➥ 16 mins to Catamount Ski Areabrbr✦BEDS & BATHS✦brInside we have 4 bedrooms and 4 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 Queen 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.brbrCleaning 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.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. brbrPlease note that the pool is only available from Memorial Day through Labor Day. Pool house (4th bedroom) is only available from Memorial Day through Columbus Day.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.

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Exceptional(1)

$539.51

/ Nightly

Private Vacation Home

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington, Massachusetts, United States

Three reasons to stay: brbr1) The Bagels – enjoy a complimentary breakfast bagel and hot beverage from the Great Barrington Bagel Company, just a mile away. br2) The Space – three fireplaces, stone pizza oven, cozy couches, and a king bed in the primary suite. Deep cleaned after each guest.br3) The Host – Berkshire-born and happy to share local tips or assist whenever needed.brbrThe Space: Located just a stone's throw away from downtown Great Barrington and minutes to ski slopes at Butternut, this charming three-bedroom house has three wood-burning fireplaces, a wood-fired pizza oven, a beautiful, well-equpped kitchen, a brick patio with outdoor seating and a Weber grill, and a fireplace in the primary bedroom. It is the perfect mix of old-world charm with modern amenities for you to unwind after a day of exploring, eating, skiing, and enjoying everything the Berkshires have to offer. brbrThe Host: As someone who was born and raised in the Berkshires, I am so happy to have the opportunity to show my guests the best my hometown has to offer. Because I am local, I am just a text/call and short drive away and can help with anything that may come up during your stay. Having a local, experienced host can elevate a lot of the unnecessary stress of your vacation and I am so happy to help! brbrNote: There is a steep driveway that is regularly plowed and salted during snowy days. While we like being honest and upfront, every guest so far reported no difficulties with the driveway. Upon leaving the property and driving down the driveway, use the mirror across the street to ensure there are no other vehicles in your blind spot.

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Sleeps

Exceptional(55)

$469.14

/ Nightly

Private Vacation Home

Minutes from downtown Great Barrington, Convenient location

Great Barrington, Massachusetts, United States

Built in 2015, this lovely 4 bedroom, 2500 sq.ft. home on a knoll is set back 175 feet from the street. This charming home offers privacy and flexibility for multi generational groups. There are 2 queen bedrooms, and 2 bedrooms with two twin beds each. The house has three full bathrooms (2 up, 1 down), a brand new kitchen with all new appliances, and a dining area which seats 8-10 people comfortably. You will also find a large living room with a gas fireplace, a separate sitting room, a laundry room, and several closets. Cable TV, wireless internet, and a land line phone are included. The house is located just a short distance from Main Street, Great Barrington. It is convenient to Tanglewood, Norman Rockwell Museum, Berkshire Theater Festival, swimming, and all Berkshire attractions. It is close to South Egremont and Sheffield for antique hunters. It is 1/2 a mile from Egremont Country Club which is open to the public for lunch or golf. It is also 5 miles to Catamount and 5 1/2 miles to Butternut Basin for skiers of all ages.

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Sleeps

$585.35

/ Nightly

Private Vacation Home

Prime Location, Recently Redesigned, Riverfront!

Great Barrington, Massachusetts, United States

Summary:brbrStay in a 4-bedroom historic factory conversion in Great Barrington. Original wood beams, stonework, and leaded glass windows highlight this riverfront Berkshires gem. Just minutes to multiple resorts like Butternut, Catamount, and Bousquet—perfect for skiing, hiking, or year-round escape.brbrbrbrThe Space:brbrStep into history with this meticulously redesigned 4-bedroom factory conversion in Great Barrington. Originally built in 1900 and tastefully modernized, this home seamlessly blends old-world charm with contemporary comfort. Nestled in the Berkshires, it offers the peaceful ambiance of a river running through the property and beautiful views throughout.brbrbrbrInside, admire the exquisite details of high ceilings, beautiful interior wood doors with lead glass, and the warmth of two wood-burning fireplaces. Natural elements like a natural rock wall and original accents in the bedrooms enhance the home's character. The living room features a grand piano, perfect for music enthusiasts.brbrbrbrThe spacious layout includes a master suite with river views and features two full bathrooms—one on each floor. One bathroom offers a deep soaking tub for relaxation, while the other provides a convenient tub/shower combination.brbrIn total, there are four bedrooms to accommodate guests during your stay, for easy planning, here are the bedroom layouts: brbrPrimary bedroom: 1 King size bedbrbrBedroom 2: 1 Queen size bedbrbrBedroom 3: 1 bunk bedbrbrBedroom 4: 2 Twin bedsbrbrbrbrConveniently located for outdoor enthusiasts, the home is a short drive from Butternut Skiing (5 mins), Catamount Mountain Resort (10 mins), and Bousquet Mountain (30 mins).brbrbrbrWhether you're relaxing indoors amidst the historic charm or exploring the nearby ski resorts and outdoor activities, this unique property offers a perfect blend of tranquility and adventure in the Berkshires.brbrbrbrOther Things to get excited about: brbr-Central AC to keep you cool!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. brbr-Full size washer and dryer available for you use. brbr-Onsite Parking for 6 vehiclesbrbrbrbrPlease 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! Standard rules like no smoking, no partying, and being respectful of the neighbors apply. No 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. Damage related to pets is not covered un the waiver.

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Sleeps

$1097.24

/ Nightly

Private Vacation Home

Stunning 6-BR Country Home 10-min to Catamount

Great Barrington, Massachusetts, United States

Summary:brbrEscape to the highlands of the Berkshires on this peaceful, 4-acre lot 10-min to skiing at Catamount and 10-min to dining and restaurants in Great Barrington. The home is newly renovated and thoughtfully appointed with 6 bedrooms, a great room with TV and fireplace, basement TV/game room, deck overlooking the rolling grounds, and a hot tub on the back side of the house. There are 4 bedrooms on the ground floor and 2 in the second floor, offering space for the whole extended family.brbrbrbrThe Space:brbrEntire home on 4 acres.brbrbrbrGuest Access:brbrAccessible with smart lock.brbrbrbrThe Neighborhood:brbrLocated on the border of Egremont & Great Barrington in the Western Berkshires, minutes to Great Barrington and Stockbridge.brbrbrbrGetting Around:brbrCar is required. Snow tires or 4x4 highly recommended during snow season.brbrbrbrOther Things to Note:brbrNotes & Disclaimers: brbrbrbrWildlife: This is a home in a rural part of the country. You may see wildlife including deer, coyotes, foxes, and bears. Please be mindful of your surroundings and leaving out food and trash. brbrbrbrWeather: In the winter, there will be snow, ice, and occasional snowstorms. We recommend driving a vehicle with AWD or 4WD. Please drive with caution and be prepared with regards to the ability of your vehicle to drive in the snow. brbrbrbrPower & Internet: This is a rural part of the country. You may lose power or internet during inclement weather. We do not issue refunds for loss of power or internet out of our control. brbrbrbrAir conditioning: There's a total of 6 AC units in the house. One window split unit + one stand-alone unit in the living-room. Also, there's one stand-alone AC unit in each of the four bedrooms. AC availability is seasonal and depending on weather (late spring and summer). Heating is also seasonal, and depending on weather, available during the cold seasons (autumn-winter).brbrbrbrPets: We're happy to welcome your pup to the home. There’s a $150 fee + tax for the first dog and $50 + tax for each additional one. If you’re planning to bring more than one, please reach out to us before completing your booking so we can get everything set up for you. For everyone's comfort, we kindly ask that dogs stay leashed outdoors and that you clean up after them. Please note that cats aren't permitted due to allergy concerns. Any pet-related damages may result in additional charges.brbrbrbrMaximum occupancy: Please mind that this house can host a maximum of 12 guests per fire code. As per the fire department, infants are included in that number. Therefore, any infants included in the booking above maximum occupancy of 12 would unfortunately result in the reservation being cancelled.brbrbrbrCancellation Policy: We cannot make any exceptions to our cancellation policy. Please consider traveler’s insurance.

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Exceptional(10)

$418.4

/ Nightly

Private Vacation Home

Family vacation home in Great Barrington

Great Barrington, Massachusetts, United States

Spacious house in excellent condition on 3 secluded acres in Great Barrington, the heart of the Southern Berkshires, available for periods from 1 to 3 weeks (1 week minimum, 3 week maximum). Rural feel, yet only 5 min from the center of town and even closer to supermarket. Skiing at Butternut within 10 minutes' drive, Tanglewood 20 minutes away. Lee outlet shopping, hiking, antique stores, etc., all within 20 min. NYC and Boston 2-1/2 hours drive. Great Barrington is a charming small town with lovely boutiques and unparalleled food stores. Winter swimming and health club at South County Community Center, a mile away.brbrHouse features screened porch with teak outdoor furniture, barbecue, and deck. 4 bedrooms, 3 with queen beds, 1 with two twins. Spacious front and back yards, woods for exploring. Living room/dining area with cathedral ceiling, skylights, multi-room air conditioning, wood-burning stove. Washer/dryer, 2-car garage, fully equipped gourmet kitchen. High-speed Internet access, TV with streaming video.

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Exceptional(7)

$434.21

/ Nightly

Private Vacation Home

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, Massachusetts, United States

Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub.brbrEnjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.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.brbrThis house is in a centralized Berkshires location with a private property featuring peaceful forest views.brbrFront door security camera (1, facing driveway), 2 small steps required for home accessbrbrbr The open floor plan of this one story cottage lets in the perfect amount of natural light to enjoy the stylish space. The spacious galley kitchen will all new appliances is stocked with everything you need for meals at home. The dining area looks in on the cozy living room equipped with many streaming services to watch on the beautiful frame TV. A washer and dryer unit is available for guest use.brbrThe two bedrooms both feature queen beds. There is a newly remodeled bathroom with a tiled walk in shower. brbrThere are 3 window AC units in the summer months, 1 in each bedroom and 1 in the living room.brbrCozy up for an evening around the outdoor fire pit, relax in the backyard hammock, or enjoy a meal on the spacious outdoor deck with a full dining set and BBQ. A partial privacy screen blocks the view of the hot tub from the street. Guests will walk through the garage to enter into the backyard.brbrVenture out for a day of winter activities. This cottage is located only 9 minutes from Catamount and 15 minutes from Butternut. Being only 7 minutes away, enjoy all that downtown Great Barrington has to offer.brbrIdeally suited for a romantic getaway with your sweetheart or a couple’s weekend escape, this updated cottage is the perfect retreat for some R&R in the Berkshires. brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbr⭐️ LOCATION: The home is centrally located in the Berkshires on a private property, offering peaceful forest views and a tranquil setting.brbr⭐️ PETS: Small dogs may be permitted with prior owner approval. No dogs under 2 years old and no multiple pets. Please reach out for approval before booking. A $100 pet fee applies if approved.brbr⭐️ PARKING: Free off-street parking is available in the driveway for up to three vehicles. Garage parking is not permitted.brbr⭐️ HOT TUB: Please keep the hot tub covered when not in use and ensure jets are turned off before closing. Guests should be aware of potential health risks associated with hot tub use and use at their own discretion.brbr⭐️ AMENITIES: Complimentary WiFi, washer and dryer, towels and linens, and toiletries are provided for your convenience.brbr⭐️ STREAMING & TV: Netflix, HBO Max, Peacock, Spectrum Cable (NYC), Hulu, Disney+, and Discovery+ are available. Please watch using the designated guest profiles.brbr⭐️ CHILDREN: This home is not baby- or toddler-proofed.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.

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Exceptional(8)

$1030.94

/ Nightly

Private Vacation Home

Luxury Retreat Minutes from Downtown Great Barrington & Ski Slopes

Great Barrington, Massachusetts, United States

Escape to the perfect Berkshires getaway! Nestled on 10 private acres and just minutes from downtown Great Barrington, this newly renovated home is ideal year-round—whether you’re here for summer by the heated pool, vibrant fall foliage, or winter skiing. Enjoy two luxurious primary suites with private balconies, a screened-in porch, and the perfect blend of privacy and convenience to everything the Berkshires has to offer.brbrPlease reach out with any questions or if you'd like to discuss booking options.brbrTwo primary suites brOne suite on the lower level with sliding doors out to a private deck overlooking the pool areabrOne suite on the upper level with a private balcony with sweeping viewsbrScreen-in porch overlooking pool areabrThree level oversized patio brHeated pool*brBuilt-in grill with barbrBuilt-in fire pitbrAttached garagebrUV light water filtration systembrbrNote: propane for pool heat will be additional cost. Pool is open Memorial Day through Labor Day.

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$367.22

/ Nightly

Private Vacation Home

Farmhouse with views nestled among nature reserve

Great Barrington, Massachusetts, United States

This preserved 18th century farmhouse is situated on a picturesque 24 acre estate boasting southerly views of rolling hills down to northern Connecticut including the majestic Mount Everett, the highest peak in the south Taconic mountains abrnd adjacent to a 900 acre nature preservation. High speed internet by Fiber.brbrThe farmhouse itself is a completely private residence with its own driveway and entrance. Originally dating back to 1788, the farmhouse was initially completely renovated in the 1940's. The property was purchased in 2018 from a 3rd generation family and lived in by the hosts then upgraded with new fixtures and appliances. brbrThe house has: on the ground floor- foyer, coat closet, an office/mudroom with closet sofa/pullout bed and desk, one bedroom with closet and dresser, one full bathroom, living/dining room with wood-burning stove, kitchen with porch and old garage space. On the second floor you’ll find two bedrooms, one with king bed and the other with a queen and a full bathroom. Plus a garage space for bikes and outdoor storage of toys!

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$412.17

/ Nightly

Private Vacation Home

Eco-Luxury Berkshire Farmhouse on Nine Acres: Toxin-Free, Solar, Car Charger

Great Barrington, Massachusetts, United States

Kick back and relax in calm & stylish farmhouse. Set on old farmstead, surrounded by meadows, stone fences, fields and forest. Featuring wonderful outdoor living on stunning nine acres. brbrGenerous mudroom, wide plank oak floors, chef's kitchen and pantry. brbrPrimary Bedroom: oversized bathroom, heated cast iron tub, walk-in closet, yoga/exercise room. brbrIn-floor heat and air conditioning. Luminous plaster walls and reclaimed timber frame add to the quiet understated luxury of this fine home. Built toxin free.brbrLet us know if you are interested in a shorter-term rental.

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$401.83

/ Nightly

Private Vacation Home

Imaginative Octogonal Glass Treehouse on Seven Private Acres near Great Barrington, MA

Great Barrington, Massachusetts, United States

This is one of the top rentals for those looking to enjoy The Berkshires in style. brbr brbrLocated near Great Barrington, Massachusetts, and sleeping four guests, this imaginative and secluded tree house rental has a queen-size bed in the bedroom, as well as a full-size bed in the living room. With its geometric, octagonal shape, this luxury rental has plenty of nooks and crannies in which to snuggle up with a new vacation read. There are two full bathrooms (one is an ensuite). Linens and towels are provided. Central Heating + AC. brbr brbrA modern wood-burning fireplace is the centerpiece of the living room, surrounded by large windows that offer glampers stunning views of the woodlands around the tree house. The dining area off the kitchen includes similar and equally impressive views of the surrounding area, as grand windows are a prime feature in this luxury tree house. The kitchen has everything a guest might need to cook their own meals, should they so choose, includes a fridge, a dishwasher, and utensils. Guests will also enjoy Wi-Fi throughout the accommodation. brbr brbrOutside, guests will enjoy their own private patio, which is a great place to enjoy a morning coffee while enjoying the views that surround the tree house. There is also a barbecue grill, perfect for a change from the kitchen and al fresco cooking and dining. There is an outdoor firepit, perfect for cozy stargazing. brbr brbrThis glamping accommodation is only one eighth of a mile from the Otis Ridge Ski Mountain with an easy hiking trail close by that leads to a beautiful pond. Access to the Knox Snowmobiling Trail at the back of the property, with ample parking outside for boats, and trailers. brbr brbrThe region boasts many cultural activities like Tanglewood, Jacob’s Pillow, and Mass MOCA.

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Exceptional(28)

$853.97

/ Nightly

Private Vacation Home

Peaceful Retreat Compound 10 Minutes to Great Barrington!

Great Barrington, Massachusetts, United States

*pool and hot tub closed for 2025, will reopen March 30, 2026*brbrPlease note that because of local laws, our minimum stay is 31 days.brbrIn one of the most sought after destinations in the Berkshires, located just outside Great Barrington near the top of Baldwin Hill where the mountains ring your view in every direction, sits a secluded three bedroom home with heated pool, hot tub, sauna, wood firepit, pickleball court, separate Clubhouse, and extensive gardens. Home has a master bedroom suite located on the first floor with a California King bed, enhanced by an expansive two-room bath with walk-in shower and beautiful soaking tub surrounded by marble-- and your hot tub and sauna are right outside via your private door. This room is equipped with its own Asko washer and dryer. Upstairs, find two bedrooms (one with a King bed and one with two Twins) and a large living room full of windows overlooking the forest. Living room has extra large flat screen TV and a gas fireplace, along with full bar area with beverage cooler, dishwasher and icemaker. Daybed with with real twin-sized mattress for overnight guest is super comfy when cuddling in for movie night! Fully modern kitchen with gas range and Perlick fridge, freezer drawers and icemaker stretches seamlessly into the family area where you will find a wood burning fireplace surrounded by windows with views of the professionally maintained lawns, gardens, and pool. Extra large round dining table seats 10+ people in comfortable upholstered chairs! All bedrooms have remote controlled exterior privacy shades on all windows. In a separate building, the Clubhouse is designed for gathering with its loft office/teen/gaming area stocked with Switch that's loaded with games, Queen sleep sofa, full bathroom, gas wood stove-style fireplace, kitchenette, and beautiful deck with outdoor gas fireplace for warmth on those chilly evenings, overlooking the woods. House and Clubhouse are modern and filled with light. Bonus Pink House with porch swing is heated and has a full fridge and a large sink -- it's the perfect spot from which to serve drinks and al fresco meals to your guests! Propane bbq for grilling near the lounge area by the pool, and on the other side of the pool is a screened in porch for dining bug free or relaxing in the shade. After a pickleball match, you'll want to take a swim in the heated pool, or head straight to the hot tub or sauna! Or just enjoy a hot shower in the private outdoor shower area. Take a long walk to the back of the 18 acre property via wide full driveway, or do as the locals do and walk to the top of Baldwin Hill. A huge expanse of the rear yard is fully fenced for your pet. In addition, there is a small pet run accessed through the one car garage, where you will also find a pet washing station and the second washer and dryer. We have both Tesla and generic car chargers installed for your convenience. Located in the quiet hamlet of Egremont, MA just minutes from everything the Berkshires has to offer! Catamount Mountain Resort 5 minutes; Lenox, MA and Tanglewood 30 minutes; Stockbridge, MA 25 minutes; Hudson, NY 30 minutes; Chatham, NY 25 minutes; Butternut Ski Resort 20 minutes, Monument Mountain 20 minutes. We provide everything you need for your stay including high quality organic linens (our mattresses are all organic too), fully stocked kitchen (including fresh spices, oils and vinegars), toiletries, pool towels, and firewood. Lightning -fast fiber optic internet with separate modems for house and Clubhouse ensures you are never offline. Whole house generator covers both buildings, so you won't be affected if the local power fails! Parking for 8+ vehicles. We pride ourselves on the cleanliness of our home. Allergy sufferers will appreciate the bare teak floors and lack of curtains, along with regular steam cleaning of upholstery. Our cleaning team uses only non-toxic and natural cleansers and our linens are free from softeners or fragrances. Air ducts, windows and exterior are cleaned twice per year, and we are happy to come by to correct any variance from a sparkling clean and comfortable home for your stay! With our local management team, we are always around the corner to assist you with whatever needs may arise. We also offer additional services such as full cleaning, daily freshening, grocery delivery, or whatever else you may need. Pamper yourself on your next visit to the Berkshires!brbrPlease note: Our heated pool will be open March 30, 2026 - September 30, 2026. Hot tub and sauna are open year round.

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Exceptional(16)

$1304.5

/ Nightly

Private Vacation Home

Swim All Day. Stroll to Dinner. Repeat.

Great Barrington, Massachusetts, United States

Bring the family, we've got the pool, the hot tub, and the table. Plenty of room to cook, or not, as it's a short stroll into town and all the restaurants.brRestored to its 1892 grandeur with high-end appliances and fixtures. Well maintained lawn and gardens. The home sits on 1.4 acres so although in town, it feels private. Huge wrap around porch, hammocks, charcoal and propane grill. 472Mbps internet. Apple tv, Steam shower, Peloton. Multiple areas to work including an adjustable height standing desk. Tesla Gen 3 (11.5kW output) charger.brShort walk to Lake Mansfield, restaurants, stores. brLinens are cleaned with Fragrance Free TruEarth eco-stripes. Non-toxic household cleaning products. No pets.brbrThe Hill is the residential area just above Main St in Great Barrington voted Best Small Town in America by Smithsonian Magazine April 2012. Big-city smart meets New England natural in an art-rich mountain setting brbrThank you for looking!

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Exceptional(2)

$1638.27

/ Nightly

Private Vacation Home

Luxuriously Comfortable Country Home

Great Barrington, Massachusetts, United States

Your Private Berkshire GetawaybrbrSet on nearly 9 secluded acres this spacious home is the perfect escape into nature. As you pass through the stone-pillared entrance, you’ll be greeted by winding stone walls, lush gardens, and towering indigenous trees—your own private sanctuary.brbrInside, the home offers 7 bedrooms and 4.5 bathrooms, comfortably accommodating groups and families. Two living rooms and two fully equipped kitchens make it easy to gather together or spread out. The highlight is a large, furnished porch, custom-designed for relaxation, where you can sip your morning coffee or unwind at sunset.brbrOutdoors, the property is beautifully appointed with fire pits, grills, and multiple seating areas—perfect for long summer evenings under the stars. A lovely nearby lake adds to the peaceful atmosphere, offering yet another spot to relax and connect with nature.brbrWhether you’re here for a family reunion, a retreat with friends, or a peaceful getaway, this home blends comfort, privacy, and natural beauty for an unforgettable stay.brWhether you’re planning a family reunion, a retreat with friends, or just a peaceful escape, this home offers privacy, comfort, and the best of the Berkshires.

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Most popular vacation rentals in Great Barrington

Exceptional(2)

$1325.32

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

Great Barrington, Massachusetts, United States

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

Great Barrington, Massachusetts, United States

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Exceptional(2)

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Lodge

Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge

Great Barrington, Massachusetts, United States

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Exceptional(2)

$3773.86

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

Great Barrington, Massachusetts, United States

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Exceptional(2)

$11193.94

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Cabin

Charming Cabin On Scenic Road

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$411.06

/ Nightly

Private vacation home

Cozy Great Barrington Home ~ 1 Mi to Ski Resort!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Great Barrington, MA

$414.13

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$367.22

$412.17

$401.83

$853.97

$1304.5

$1638.27

Rent a place that suits your needs

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