Home Vacation Rentals By Owner In Great Barrington, MA

Showing 92 Of 92 Vacation Rentals
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$585.35

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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.
Bed 4

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Bath 2

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Sleep 8

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$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.
Bed 6

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Bath 3

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Sleep 12

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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.
Bed 2

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Bath 1

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Sleep 4

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$401.83

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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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Bath 2

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Sleep 4

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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.
Bed 4

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Bath 3

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Sleep 12

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