Vacation Rentals By Owner In Great Barrington, MA

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

Cabin

Luxe Log Cabin Minutes From Skiing, Hiking, & More

Great Barrington, Massachusetts, United States

3

Bed

Bath

10

Sleeps

$136.82

Stay in a secluded log cabin in the woods! Our rustic, comfortable and welcoming cabin is a perfect getaway from city life. Enjoy all that the Berkshires have to offer from a quiet hill just outside the hubbub of town. Our sweet cabin is available for longer term rentals. brbrWith amenities, such as electric heat, hot running water, and a full bathroom, your stay will be comfortable.brbrOur cabin sits on a forested plot at the top of a hill in beautiful Great Barrington. You cannot see other houses when the foliage is out so it is very quiet and private. brbrWe are located about 2 miles from downtown Great Barrington. The area has a variety of delicious cuisine options. There are plenty of shopping and galleries in the area. There are several grocery stores and a fantastic food coop. brbrIt's easy to walk down the hill to some restaurants and shops (about 15 minutes). Hearty folks can walk back up the hill (about 30 minutes). brbrThe Appalachian trail is nearby along with plenty of other beautiful hiking trails. We are under 10 miles from Beartown State Forest.brbrWe are just a hop, skip, jump from world class attractions such as Tanglewood, the Norman Rockwell museum, Kripalu, Jacob's Pillow, the Omega Institute and a ten minute drive to Butternut Ski Resort. Enjoy all that the Berkshires have to offer from this cozy log cabin!brbrOur parents built this log cabin in 1976 and it still has the classic rustic vibe. The circular staircase is in the center of the cabinbrbrThere are two bedrooms upstairs and a downstairs bedroom with a loft bed that can be used for an office. brbrThe kitchen is fully equipped and the fridge is brand new. The stovetop has some damage but works like a gem. brbrThere is a unique wooden dining table with benches built when the cabin was built. brbrThe cozy living room has a large window and four other windows along with a woodburning stove.brbrPlease be aware:br-We do not have laundry on the premises. br-You will need to bring your own linens (sheets, pillow cases, towels, kitchen towels etc.) br-We have a problem with bears and the garbage so you will need to take your garbage/recycling with you or there are a couple of other options we can tell you about.br-Woodburning stove can be used with permission. You must purchase your own wood.

Cabin

Log Cabin in the Woods with a Rustic Vibe

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$651.74

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 and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn`t rectified. 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.

Jug End Crest | Fireplace • Sunroom • Central Air

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$558.5

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

An In-Town Beauty with Late Checkout

Great Barrington, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$1288.69

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

Renovated family friendly house close to everything and endless views

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$662.62

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

Cozy escape in the trees of the Berkshires

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$361.43

Cozy yet expansive 3 story home within 15 minutes of Lenox, Stockbridge, Tanglewood, Great Barrington, and Catamount and Butternut Ski Slopes. Wonderful central location for exploring the Berkshires for winter skiing. Recently renovated with private 3rd floor master suite including a study, this home is perfect for a long weekend getaway. brbrTwo bedrooms on the ground floor allow for privacy between adults and children. The middle floor has full kitchen, dining area, living room and TV/game room, and a wood-burning stove.brbrThe open deck and screened porch are perfect for outdoor dining or cocktails by the lake. There is a canoe and rowboat for fishing and in the winter you may actually see ice fisherman. brbrWi-Fi access, Satellite TV, upstairs and downstairs washer-dryer, A/C, heat pumps, electric baseboard heating, and whole-house exhaust fan.

Just You, the frozen lake, and 2 nearby ski areas! Perfect cozy winter getaway

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$184.89

Greetings from the Serendipity Spot where old meets new in this charming, elegant & peaceful space where you may rest, laugh & play in the beauty of The Berkshires. Nestled in Great Barrington, this convenient spot has easy access to hiking, skiing, cultural events and restaurants galore. We are a 15-minute drive to Tanglewood and Shakespere & Co in Lenox, 12 minutes to the Norman Rockwell Museum in Stockbridge, 13 miles to Jacob's Pillow, and Ski Butternut is around the corner 2 miles away.brbrThe spacebrIn this upstairs suite, you will find a cozy love seat, games, coffee and tea bar, and a flatscreen tv to unwind. The stylish bathroom sports a rain head shower and a heated floor furnished with plush towels and robes. The bedroom has a delicious Queen bed with black-out blinds to ensure your restful sleep. The suite is equipped with Wi-Fi and bedside plugs for all your devices.brCome enjoy The Serendipity Spot and explore all that The Berkshires has to offer. Leave rested, restored, and rejuvenated!brbrGuest accessbrThe suite is connected to our home. Although there are shared walls in the living room, the suite has its own private entrance and is otherwise completely private.

Apartment

The Serendipity Spot

Great Barrington, Massachusetts, United States

1

Bed

1

Bath

Sleeps

$379.78

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

Berkshire Summer Retreat - 3 bed/2 bath

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$826.58

A lovely property with gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood & Jacob's Pillow. 5 bedrooms (6 beds), 3.5 baths, sleeps 12. The main floor has an open floor plan, making each room flow into another, including a spacious living room with a large smart TV, a fireplace pellet stove, an upscale & fully equipped kitchen, half bathroom, a dining area which opens to a deck with breathtaking view and a screened porch. The main floor also houses a master bedroom with a king size bed, an attached master bathroom (with deep bath-tub & a separate shower) and an office in a separate room. The upper floor has a bathroom with tub & shower and two bedrooms: one with king size bed, and the second bedroom has two queen beds (sleeps 4). Downstairs floor has 2 bedroom (one has attached full bath), and laundary/exercise room. The backyard has a large blue-stone paved patio, where you can recline, enjoy the view, barbecue, or sit by the fire pit to roast marshmallows. The house sits on 0.8 acres land is surrounded by trees to provide privacy. Enjoy the use of: 4 kayaks & 1 Canoe (you can roll it on an attached cart) to Lake Mansfield boat dock which is 300 feet away. This property is perfect for families, vacationing couples, or group of friends. House has central heating, AC units, smart TVs (in living room and all bedrooms) and high-speed internet access.

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

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$681.02

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

Berkshires Retreat with Fall Foliage, Views & Cozy Fireplace Near Town. nn

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$523.84

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

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$3773.86

A breathtaking estate nestled on a mountain slope of granite in the Berkshires. Immerse yourself in 120 acres of natural wonders & wildlife. A private oasis that delivers inner peace & rejuvenation. brMain house: 7 bedrooms and 8 baths plus 3 private rooms that can be converted into luxurious bedrooms for a small feebrGuest house: 2 bedrooms and 1 bath (extra cost)brBarn: 3000 sq ft (extra cost)br* 14.75% MA state tax paid by guestbrThe spacebrPricing and capacity:brPricing on this site is for main house up to 14 people. The entire property which is 11K square foot includes 7 bedrooms in the main house with 3 additional private rooms that can easily be converted to bedrooms. We also have a guest house on the property with 2 bedrooms, a full bath and a living room and kitchenette and a 3,000 square foot barn which has a lounge/ loft, kitchen, 2 showers, washer and dryer, a basketball hoop and ping pong table. The barn and guest house are rented separately, so you have the choice to rent them all or just rent the main house.brbrA vacation paradise for all seasons, long pond 250 has it all. If you are looking for a winter holiday, long pond is a short 15 min drive to the kid friendly butternut and Catamount ski resorts. After a day of skiing (or in lieu of), retreat to our oasis in the mountains and enjoy sledding on the property, sip hot chocolate and barbecue marshmallows around our beautiful firepit and end the evenings by cooking in our chef inspired kitchen with a glass of wine by one of the indoor fireplaces. Don't forget to top it off with a quick dip in the hot tub on the porch in the summer spring or fall! If you are looking for some downtime and don't feel like being in the kitchen or cleaning, we have a host of wonderful local chefs and service providers in the area.brbrIn the summer, the pool is wonderful, the surrounding area lush and green. We have hiking/mountain biking trails on the property, and can arrange mountain bike rentals. The pool and hot tub are closed from September to May. brbrHot tub is extra $600 charge as it needs to be cleaned and prepped between guests.brGuest accessbrThere are several dwellings on the property as well as 120 acres. Inquire about what is included.brbrParties and eventsbrUntil further notice, all disruptive parties and large events are prohibited regardless of size.

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

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$822.0

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

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$244.98

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

Cottage

Berkshire Mountain Cottage: in the Heart of the Berkshires

Great Barrington, Massachusetts, United States

Bed

1

Bath

4

Sleeps

$412.17

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.

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

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$468.4

Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This rustic 4-bed, 2-bath home is complete with woodsy-style decor, contemporary furnishings, and space for 10. It's truly a sportsman's paradise - tucked away in the woods on Round Pond, where you can hike, fish, swim, boat, or admire it all from the deck and dock. Whether you're here for summers at the Symphony, winters on Ski Butternut, or leaf peeping in the fall, Great Barrington has it all.brbr-- THE PROPERTY --brbrBedroom 1: Full Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed | Bedroom 4 (Loft): Twin Bed with Twin Pullout (Can be converted into a King), Full BedbrbrYou'll find this rustic property hidden away in a semi-remote, wooded area, with very few neighbors nearby. Mornings here offer incredible views and quiet surroundings - best enjoyed with a warm cup of coffee on the deck.brbrThis property is located right on Round Pond. With crystal clear water untouched by busy beaches or motor boats, this lake is ideal for swimming and fishing! Take a dip off the dock, or venture out on the rowboat provided.brbrAfter a day on the lake, head inside to enjoy some downtime. The living room is complete with cathedral ceilings, floor-to-ceiling views, and a cozy wood-burning fireplace, altogether creating the perfect place to unwind.brbrEnd the day with a hearty meal made in the fully-equipped kitchen. Follow dinner with a sweet treat of s'mores by the outdoor fire pit!brbrWhen you're ready to retire for the night, 4 bedrooms offer space for up to 10 guests.brbr-- THE LOCATION --brbrNamed as the #1 best place to live by Smithsonian Magazine, Great Barrington is a small-but-mighty town brimming with activities and charm.brbrTake some time to tour the Berkshires. Within 15 minutes you'll be able to hike across Monument Mountain, shop and dine in Great Barrington, stop by the Norman Rockwell Museum in Stockbridge, or test your winning streak at the Springfield Casino just 40 minutes away.brbrThe famous Tanglewood lies just 10 miles away. Since 1937, Tanglewood has served as the summer home for the Boston Symphony Orchestra. Concerts here will take your breath away!brbrThe Berkshires turn into a winter wonderland when the snow falls. You'll find multiple mountains within 10 minutes of the property, including Ski Butternut and Catamount Ski Area, with Bousquet Ski Area, Jiminy Peak, and more just a short drive further!brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- Massachusetts Tax ID: C0198611130br- No smokingbr- Pet friendly w/ $75 fee (+ fees & taxes, dogs only)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There is a completely separate unit located next door with its own private entrance. Other guests will not be present however the separate unit is off limitsbr- NOTE: This unit also has exterior-facing cameras, but they do not look into any interior spaces of the vacation rentalbr- NOTE: The property requires stairs to accessbr- NOTE: The property does not have air conditioning

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$492.56

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.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$986.27