Vacation Rentals By Owner In Great Barrington, MA

Summary:brbrNewly renovated three bedroom “on the hill” in Great Barrington awaits your next family stay. Short walk to downtown Great Barrington for dining, easy stroll to Lake Mansfield for swimming or fishing, and walking trails. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 3 minute walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more!brbrbrbrThe Space:brbrEnjoy all day sunlight in this Berkshire gem which is set 100 feet off the road in it's own private setting. Watch the sunrise over the mountain trees while you have your morning coffee and breakfast on the lounge deck off the kitchen. As the sun rotates around the house throughout the day so can you from the kitchen deck to the deck off the living room to enjoy outdoor dining, BBQ, and a gas firepit. In the evening you can choose to also enjoy the wood fire pit with views of town, the mountains, stars, and a rising moon.brbrbrbrChef’s kitchen complete with a seamless 10 foot quartz countertops that seats 5, gas stove with range hood and microwave. The quiet dishwasher makes cleaning up a breeze. It’s an eat-in kitchen with space for five at the counter and eight at the dining table with views of the mountains and great sun and moonlight.brbrbrbrJust beyond the kitchen is the living room with a decorative fireplace. Plenty of seating with designer leather sofas and accent chairs. Large smart tv so you can log into your streaming apps or there are plenty of cable channels through Sling. The house is stocked with games that the family will enjoy which you can play at the kitchen table, island, lounge seating area, or TV seating area. While someone is watching TV you can be in the lounge playing games but also enjoying the company of everyone else.brbrbrbrSpace for up to eight guests, here is the bed layout for easy planning:brbrBedroom 1: king size bed in the main bedroom with streaming capability tv. Tufted Needle memory foam mattressbrbrBedroom 2: two queen size beds - 12 inch memory foam mattressbrbrBedroom 3: one queen size bed - 12 inch memory foam mattressbrbrbrbrTwo fully renovated bathroom with shower/tub combo. Rain shower head and handheld for convenience for showering or bathing.brbrbrbrThe home is a peaceful retreat with mountain views out front and on the sides. Sit outside and enjoy the Berkshires with your outdoor dining area, cook up tasty meals using the bbq gas grill or kitchen, and enjoy the evening either by the wood fire pit or the gas fire pit. You will see wild life including deer, foxes, birds, hawks, and lots of nature sounds with great flowers. This quiet yet centrally located home is a peaceful escape while being close to the action. Lake Mansfield is a few minutes around the corner where you can find a beach and dedicated swimming area with a lifeguard on duty certain days and times. There are picnic tables and BBQs, fishing areas (catch and release), and a nice flat manicured walking trail through the woods.brbrbrbrOther amenities worth noting:brbr-Central heating to keep you warm this winter.brbr-All the bedrooms, living room and kitchen all have window-unit AC to keep you cool during summer months.brbr-Wide plank pine floors in the living spaces and rugs in the bedrooms.brbr-Easy one floor living, easy path to the front door then a single step to get into the house.brbr-Laundry room with washer and dryer.brbr-Fast wifi throughout the house.brbr-Parking for up to 6 cars,brbr-All mattresses are memory foam with cotton sheets and a comfy down alternative duvet and four pillows.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrGuest Access:brbrEverything you need for a great stay, toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!brbrbrbrThe Neighborhood:brbrWalking distance (~2 mins) to downtown and all the great restaurants/shops that Great Barrington has to offer.brbrbrbrWalk to hiking trails and the lake from the house or take a quick 5-10 minute drive to many more hiking trails in the mountains and lakes.brbrbrbr20 minutes to Tanglewoodbrbr15 minutes to Lenoxbrbr10 minutes to Stockbridgebrbr5 minute drive to Ski Butternutbrbr20 minutes to Catamount Skiingbrbr30 minutes to Jacob's pillowbrbr25 minutes to Bish Bash Fallsbrbr20 minutes to Becket hiking areabrbrMuch more - check out our guide for more suggestions and things to do!brbrbrbrGetting Around:brbrYou can arrive and park your car and then walk to everything you need from grocery stores, convenience stores, shopping, restaurants, coffee, bars, and much more! Or a short drive will get you to everything you need and more.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no pets, no smoking, no partying, and being respectful of the neighbors apply. Security cameras located in the driveway, and the front and rear entrances.brbrbrbrIf you are booking through VRBO: You agree that The Host will charge your card for the full payment of the stay 24 hours after booking. Any payments by VRBO (service fees) will be charged separately. brbrbrbrDamage: 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.

Renovated Downtown Great Barrington House

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$1647.89

Rosecliff Amenities: Main House, Heated Pool with Pool house, Sleeps 13 in beds or 15 max. high speed WIFI internet and good cell service, Smart TVs with Streaming TV channels, central AC throughout, several areas for outdoor seating, sun umbrellas, (2) propane grills, mountain views, all high end appliances, sun room, washer/dryer (3), several gas and wood burning fireplaces, attached garage, easy access to all Berkshires venues - close to both Butternut and Catamount, less than 5 mins to the center of Great Barrington. NO smoking, please.brbrWelcome to Rosecliff! We are so happy to present this exceptional Berkshire estate that includes the main house, heated pool, and pool house. The main house has 5 bedrooms with 5 ensuite bathrooms plus 2 half baths and sleeps up to 11 in beds or 13 max (with an additional sleep space sofa bed). The pool house sleeps 2 more guests with another full bathroom and is fully heated, and cooled, and can be made available year-round. The main house is 9,500 sq ft. This property is so lovely and has so much to offer. The house sits back far from the country road and is welcoming the minute you pull in. brbrThe main floor has a entry that leads into the bright open kitchen. The appliances are all stainless, with plenty of storage, gadgets and prep space that offer guests a premier cooking experience - whether they want to create their own meals or bring in a local chef. There is a large farmhouse style table for casual dining and another gracious dining room, with a cozy propane fireplace, for more formal gatherings. The kitchen has big meadow views and is sun-filled. There is a small sitting area between the kitchen and dining room that offers a cozy space, with a full wet bar consisting of a dishwasher, ice maker, sink and wine cooler. Continue past the dining room to the large living room with another fireplace and plenty of seating. There is a cozy media room with a large TV for streaming all your favorite channels. There is still more to enjoy on the main floor with a summer sun porch and another parlor for easy gatherings, with seating and beautiful views. Just outside, on the covered patio is a lovely set up with seating and a grill for taking in the late afternoon views and sunsets. brbrUpstairs you have all 5 bedrooms - each with ensuite bathrooms - plus an additional bonus Playroom that has a fold out sofa for another guest or 2. This area has its own entrance through the back staircase and has another large TV, an efficient kitchenette with microwave, fridge, and coffee maker, etc. It also has its own full bathroom, with a shower. This is a terrific kid's space for TV viewing, gaming and is perfect for a nanny or babysitter. brbrThe 5-bedroom suites are fabulous - each with its own style and attention to detail. The primary is grand with beautiful views, a king bed, sitting area with gas fireplace and its own TV, a large dressing area and the best primary bathroom around - with a huge walk-in shower, soaking tub, 2 sinks and another sitting area. Guest room #2 has another king bed and its own brick gas fireplace. The ensuite bathroom has a luxurious clawfoot soaking tub and a walk-in shower. Guest room #3 has 2 Twin beds, built-in closets and drawers, and an ensuite full bathroom with a tub/shower combination. Guest room #4 overlooks the pool and has a Queen bed and a Twin daybed so 3 can easily sleep here. This ensuite bathroom is a “Jack n Jill' style and shares with guest room #5. The bathroom has its own walk-in shower and another glorious soaking tub. This beautiful bathroom also has a small Juliet balcony. Guest room #5, also overlooks the pool, has a Queen bed and its own TV. The bonus playroom is located on the second floor, up the back staircase, and can also be accessed on a roof deck off the primary bedroom and guest room #2. It has another TV and is a great space for kids as well as a Queen sofa bed for added guests and has its own kitchenette. brbrThe Pool house, located less than a minute's walk from the main house (heated, also with AC) offers another option to guests with a king bed, sitting room with mountain and meadow views, has its own kitchenette, TV, and full bathroom with walk-in shower. There is another terrific full kitchen just adjacent to Pool House, known as the “Cook Shack”. This area has its own fridge/freezer, range, dishwasher, utensils, set ups, etc., and another bathroom so there is no need for swimmers to drip water into the main house or pool house. brbrOutside, there is so much to enjoy here on this 16+ acre spread. The heated pool has plenty of both lounge and table seating, umbrellas for shade, another grill, and striped pool towels are included. The pool has easy access to the pool house and cook shack. The lawn is vast and lush and offers plenty of run-around space. There is a marvelous outdoor seating area just outside the kitchen with a stone patio, grill, ultra-lux seating and a fire pit. This is a stunning way to end the day, overlooking mountain and meadow views. brbrLocation: Rosecliff is less than 5 minutes to the center of Great Barrington, less than 15 to Ski Butternut and less than 10 to Catamount. And, just about 30 minutes to Tanglewood. Rosecliff offers our guests everything possible in a luxury retreat with close access to all the Berkshire has to offer. brbrMain House Guest Room Bed and Bath Recap : sleeps 11 in beds or 13 maxbr(All on second floor):brPrimary Ensuite: King bed, soaking tub, and oversized walk-in shower.brBedroom #2, is ensuite: King bed, shower and soaking tub.brBedroom #3, is ensuite: 2 twin beds, with tub/shower combination.brBedroom #4, Queen bed and twin daybed.brBedroom #5 has a Queen bed.brGuest bath is shared, Jack 'n Jill style between Guest rooms #4 and #5brbrBonus Playroom has a kitchenette, full bathroom (tub/shower) and a Queen foldout bed.brbrPool House: Sleeps 2 more guests in a king bed, kitchenette, and full bathroom with shower.brbrTotal sleep capacity in beds is 15.

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

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$364.7

{STAND ALONE UNIT}. Central and Private!! brJust steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy sunset views with friends and family before you walk into town for a night out! brThis brand new home features all new appliances and furniture. brEnjoy the comfort, charm, and privacy of home while you rest easy at the Maple. P.S. 413/717/7240 feel free to call at any reasonable time for questions. Always call at any time with an emergency. I’m here to help. Thanks

Home in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$529.33

NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street name.)brbrBOOKING FOR THE REST OF 2025 AND THROUGH 2026! brbrAfter a fully booked summers through 2024 and mostly booked for summer 2025 (a few spots remain open!), we are booking for the remainder 2025 and all of 2026. We are excited to see returning guests as well as new ones. brbrOur five bedroom, three bath, two fireplaces, and two large 'family' rooms are ready for you and your guests. Almost three acres of property give you privacy, but you are less than 2 miles from Great Barrington, 5 minutes from Ski Butternut, and inches away from a spectacular views of New England 'country' life. Local restaurants for all tastes abound, our kitchen has all the implements you need for staying at 'home' for a meal. brbrAnd the house you'll be renting - about that:brbr A week, a month, a weekend, or a few days in the beautiful Berkshires - - what could be better Located 130 miles from NYC and from Boston, this “rustic” yet modern beloved family vacation home in the heart of the Berkshires is available year-round. With five bedrooms and three full bathrooms this house easily sleeps 10 in bedrooms, with another double futon in the family room, and plenty of room for extra visitors as you wish. Seat 10-12 around the dining table, in the screened-in porch, or on the spacious deck overlooking the 20 x 40 in-ground pool (closed mid-September until Memorial Day weekend). Ready for campfire time We have a fire pit all ready for you. Renovated kitchen with new refrigerator and dishwasher is fully equipped for indoor cooking as well as the outdoor gas grill. On those cool or cold nights, cuddle up in front of one of two wood-burning stoves (in the family room or in the living room.) Living room also has a two-story cathedral ceiling with floor to ceiling windows overlooking the pool and yard. Privacy abounds on our 3 acre lot, but access to Great Barrington is easy - 1.6 miles away! When the pool is closed (it is unheated - so you want it closed off-season!), you still have two family rooms, two wood-burning stoves, a Jacuzzi tub and more to relax; you can shoot pool, play games, stream movies, watch tv, and spend time catching up on your reading and fun. Plenty of books, games and puzzles available for your use. Have little ones We can supply portable cribs, high chairs, bedguards and even potty-trainers! We even have a toddler 'playground' out back (turns out our grown kids don't need it any more. Been there, done that!)brbrFive bedrooms include two 1st floor bedrooms (one with a double bed, one with two twin beds that can be made up as a king-size bed), two 2nd floor bedrooms (one with a double bed and one with a brand-new queen! and a primary suite above the family room at the opposite end of the house. Primary suite has king-size bed, two walk-in closets, and a bathroom with double-nozzle shower and separate Jacuzzi tub. There are two additional shared full bathrooms in the main part of the house, one downstairs and one upstairs. Hair dryers provided. You'll stay warm (and cool, as appropriate) with our ductless heat pump heat and air conditioning systems throughout the house - every room has individual thermostat controls if you need heat in addition to the heat pump systems and wood stoves (we are fully stocked with firewood!)brbrFirst-floor laundry room with full-size washer & dryer and closet rod to hang freshly laundered clothes and a tiled floor to dry out your skis and boots. Ironing board and iron provided. Linens provided. Beach towels & pool play toys provided. brbrElectronics: Wi-Fi, Cable TV (Spectrum), 5 Televisions ( all Flat Screen), and strong mobile phone service. brbrReady to leave the house It’s hard… but the house is less than 2 miles from Great Barrington with its restaurants and shops, 3 miles from Ski Butternut, 6 miles from Norman Rockwell Museum, 6 miles from Stockbridge, 10 miles from Tanglewood Music Festival (summer season), Jacobs Pillow Dance Festival (summer season), 11 miles from Lee Premium Outlet Mall, and more. Lakes, ponds, hikes, and walks. Whether you prefer hiking a portion of the Appalachian Trail or nearby Bish Bash Falls (Massachusetts highest waterfalls), or visiting Ashintully Gardens in Tyringham to fly fishing in local streams - so many wonderful outdoor activities. The Audubon Society's Pleasant Valley Wildlife Sanctuary's 7 miles of trails through their 1,132 acres in nearby Lenox, and you can go taste fresh maple syrup at Ioka Valley Farm's cafe. More of an indoor fan - how about a spa visit or yoga class (or two) at the Kripalu Center or Canyon Ranch in Lenox Looking for the 'arts Edith Wharton's beautiful home in Lenox, The Mount, is only a few miles away, another Victorian home Ventfort Hall, was built by the Morgan family (of JP Morgan fame) and is now open for to visitors. Of course the restaurants are open, the Triplex Cinema in Great Barrington is showing first run and classic films, the art galleries and antique shops await you. So much to do and see.brbrPortable lawn chairs provided to take on family outings (e.g. to Tanglewood Music Festival). brbrOutdoor shed with room to park bicycles or sleds you might bring.brbrThe beauty of the Berkshires is year-round – and this house can be your home-base for all of it. brbrPlease note: If you are looking for a Hamptons-like mansion, we hope you find your dream vacation home. This isn’t the one. If you want a place that you can play, eat, sleep, relax, spread out and enjoy – we hope you give our home a try!brbrQuestions Let us know! We will be providing an extensive guide to the house and area for your stay - but in the meantime, ask away. If we don't know the answer, we'll find out for you!

5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$1004.51

Luxury 4-Bedroom Retreat | Hot Tub • Pool Table • Gym • Spacious deck & lawn.brWelcome to your private getaway — a beautifully designed 4-bedroom, 2-bath luxury home that blends comfort, style, and upscale amenities for a truly unforgettable stay.brUnwind in the outdoor hot tub under the stars, challenge friends and family to a game on the full-size pool table, or keep up your routine in the fully equipped fitness room. Whether you're gathering in the open-concept living area or relaxing outside on the expansive deck, there’s space for everyone to feel at home.br 4 Comfortable Bedrooms – Thoughtfully furnished with quality linens and stylish decorbr 2 Modern Bathrooms – Clean, elegant, and fully stocked with essentialsbr Large Private Lawn – Perfect for outdoor games, lounging, or enjoying your morning coffeebr Hot Tub – Your own private spa experiencebr Pool Table – Great for friendly competition or casual evenings inbr ️ Fitness Room – Includes cardio and strength equipment for daily workoutsbr ️ Fully Stocked Kitchen – Ready for cooking, dining, or entertainingbr Fast Wi-Fi & Smart TVs – Stay connected and entertainedbr Free Parking On-SitebrLocated in a peaceful neighborhood, you're just a short drive from [local attractions, restaurants, or nature spots], making this the perfect home base for families, groups, or professionals seeking a stylish escape.brWhether you're here to relax, explore, or celebrate, this home offers the comfort of a boutique hotel with the privacy and warmth of a personal residence.

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington, Massachusetts, United States

Bed

2

Bath

Sleeps

$595.73

Great Barrington is waiting for you at this lovely historic country cottage. With one king bed and four twin beds, it’s perfect for families or groups. The cottage features two bathrooms, each equipped with a hair dryer for your convenience. Guests will appreciate the comfortable heating and cooling options that keep the space just right year-round. Whether you’re relaxing indoors or exploring nearby, this beautiful cottage is nestled between 2 ski mountains ( Butternut & Catamount), and close to Tanglewood, Shakespeare & Co and Jacobs Pillow. This is a superb home base. Enjoy all that Great Barrington has to offer when you stay at our place.

Cottage

Charming historic country cottage on 7 private acres near Tanglewood & skiing

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$223.04

Located between the villages of Stockbridge, Housatonic and Great Barrington. Most unique Riverhouse property located on the bank of Rising Pond of the Housatonic River.brbrBuilt around 1860, the Riverhouse has been updated and outfitted for modern-day convenience but retains its charm and unique appeal. From original painted-board floors and claw-foot bathtub with shower to modern amenities this property offers spectacular views of foliage and wildlife from the deck, picture window and bathroom of this upstairs artist’s aerie, filled with original art by local artists.brbrThe only house located directly on the banks of Rising Pond of the Housatonic River, it offers spectacular views of fall foliage and wildlife and makes for an authentic Berkshires experience. Spectacular sunsets every night. Easy access from the bank of the property for small boating and sculling. Located in the heart of the Berkshires; the Appalachian Trail, Tanglewood, Shakespeare and Co., the Rockwell Museum, Chesterwood, summer stock theater, music, and dance are all just minutes away. Easy access to Butternut Ski 5 miles and Catamount 12 miles. Fully equipped kitchen with all cooking utensils and serving dishes make eating on the deck and entertaining a delight. Walking distance (1/4 mile) to the fabulous Berkshire Mountain Bakery with delicious french pastries and bread for your morning coffee and take away pizzas for easy meals. Taft Organic Farms is 1.25 miles down the road for delicious local products, produce, sandwiches, farm animals and more.brbrThe open floor plan and lovely views make this efficient upstairs apartment seem much larger than it’s 650 square feet. The two private bedrooms include a king bed that can be made into twins in the first and a queen-size bed in the second. The large bathroom features an antique full-size claw foot bathtub (with shower) that gives out to a incredible view as you soak! Full laundry facilities available. Kayak and small boat access from from river bank. Bring your boat! Parking for two cars. There are 13 steep stairs to the apartment and the claw foot tub is tall. This apartment is NOT ACCESSIBLE.brbrSmithsonian Magazine has voted Great Barrington one of America's 20 Best Small Towns! Find out for yourself...a hidden gem. So many wonderful things to do and things to eat in the immediate area...brbrhttps://www.thrillist.com/travel/new-york/things-to-do-in-the-berkshires-massachusettsbrbrFeel free to contact me directly for information and reduced rates for extended stays by way of Ask Owner a Question located under Request to Book where you can find my email address. brbrHigh summer season rates: $200/night 7 night min.br$1400/weekbrLow season (September-end May): $175/night. brbr Rate changes for some holidays to $200. See calendar.brLeaf peeping, Christmas, New Years: $200/night (3 night min); $1225/week.brInquire about longer term rates ((monthly).br$120 cleaning feebr$500 refundable security depositbrbrNo refunds for cancelling unless we are able to re-book the dates. Guests reserve months in advance for high season and we lose many opportunities to book when we take your dates off the calendar. We hope you can understand our position.brbrPlease check out our sister property:brVRBO#759695 brThe Blue House on the Bendbr3 bedrooms/2 baths on a beautiful bend of the Housatonic river! Sleeps 5brAnother fully-equipped, beautiful property that will easily accommodate 5 more if you are traveling with a larger group and need more space and/or more privacy.brbrbrKeywords: Stockbridge, Housatonic, River house, Great Barrington, Housatonic, upstairs apartment, spectacular view, 2 bedrooms, Tanglewood, Berkshires, unique property, river view, water view, sleeps 4, full kitchen, Butternut, Catamount, Kripalu, Charcoal grill, sunset view

Apartment

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

Great Barrington, Massachusetts, United States

2

Bed

1

Bath

Sleeps

$1135.62

Well appointed Vacation Cottage, newly renovated by the Owners; An Architect and an Interior Designer as a Modern Farmhouse. br5 bedrooms, 4 bathrooms, 2 large living rooms, an entertaining playroom and a well-equipped Kitchen, Front and Rear covered porches w/ a Hot Tub overlooking the open forest view.brThe large open lawn hosts volleyball net, soccer goals, picnic tables with lighting for outdoor dining, Solo fire pit sitting area, BBQ grill and yoga matts for your early am flow.brThe Hot Tub for 5 is conveniently located under the covered rear porch overlooking the forest. 5 min drive from Lake Mansfield and the town of Great Barrington and other beautiful surrounding hiking trails.brComplete privacy yet only about 10 min drive from 2 Ski resorts, Butternut & Catamount. 5 min drive from Lake Mansfield and the town of Great Barrington and other beautiful surrounding towns with many options for Restaurants, Shopping, Balling Ally’s, Music & Theatre events and festivals & hiking trails, one would never get bored. brbrClimbing only 3 steps to the front deck, entering the house into a double ht. foyer that leads to an open floor plan brbrThe house is fully air-conditioned/heated with ample storage and closets for shoes, ski gear and coats. Walking into an open floor plan; Kitchen, Dining & couched Fireplace sitting area & Living Rooms.brbrThe kitchen is fully equipped and has an eat-in island (sits 5). The dining table is large enough to for great family and friends gatherings.brbrThe house has 2 separate large Living Rooms, each equipped with 75” HD smart TV and large sectional sofas.brbrThe playroom includes a full size double Pop-A-Shot (double hoop basketball game), Air Hockey table, a Foosball table, XL Janga, Remi cube, Bingo and other board games.brbrThe Laundry room equipped with 2 Washer machines and 2 Dryers.brbrThe 2nd floor includes a Yoga space / Sitting area overlooking the forest, 2nd Master bedroom, oversized King room with office space and anther bathroom with tub. brbrBedrooms:br#1 - Master Bedroom #1 - On First Floor - Queen size bed with private oversize bathroom & jungle shower with 2 windows overlooking the woods while you shower.brThe Bedroom includes a comfortable armchair & side table, light night, closet and dresser.brbr#2 - Master Bedroom #2 - On 2nd Floor - Queen size bed with private bathroom & jungle shower. brThe Bedroom includes a comfortable armchair & side table, 2 light night, closet and dresser.brbr#3 - King Bedroom - On 2nd Floor - Extra Large bedroom with a King size bed and a pull out twin bed and a twin open sofa The room has an eclectic collection of furniture to provide comfort and function with a reading nook. The Bedroom includes a comfortable armchair & side table, light night, closet and dresser.brThe full bathroom with a tub is across from it. brbr#4 - Queen Bedroom - Queen size bed with a built-in loft over it with a twin mattress. The Bedroom includes a side table, light night, closet andbrDresser.brbr#5 - Bunk Bedroom - Sleeps 4 on twin size mattresses on 2 bunk beds. The Bedroom light night for each bed personal cabbie unit for each of the 4 guest.brbrThe 4th full bathroom is located on the first floor.brbrEach Queen bed has 4 pillows (2 down pillows and 2 alternatives and a down comforter).brbr- An Office / Open Gallery Space is located on the upper floor with a sofa and a trundle bed under it, providing additional two twin size sleeping beds arrangement.brEach guest gets 2 large towels. brImportant highlight features - Covid prevention Committed, Completely fenced backyard, private parking spaces, Strong WiFi, the house is Fully Air-Conditioned.brbrNight light for each bed and Designated storage space for each of the guestsbrEuropean comfort - all bed linens are are 100% Cotton/400-600 thread.brDown pillows & white goose Down comforters.brbrThe Cottage has an Alarm system and security cameras that are directly connected 24/7 Fire & Police departments. Outdoor Solar lights around the back yards. And a smokeless fire pit (Solo) & Hot Tub for 5.

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington, Massachusetts, United States

5

Bed

Bath

16

Sleeps

$879.7

White Birch amenities include 4 bedrooms, 3 baths, Sleep 12+ a main floor master suite with a large walk in shower, hot tub, high speed internet, 5 Smart TVs with access to streaming channels like Netflix, etc and a Sonos sound system, Ping Pong, Foosball table, Nintendo Wii, mini-split wall unit air conditioners, brand new appliances including a gas range, washer/dryer, EV car charger, standard drip coffeemaker, and a dishwasher. Outside you will find beautiful mountain views, a fire-pit, outdoor seating, propane grill and the Appalachian Trail that is only a short walk down the road. The home is located only 10 minutes to Great Barrington, 15 minutes to Stockbridge, and 25 minutes to Tanglewood. Pets are considered with a $150 pet feebrbrMain Floor: This perfectly renovated, open concept home is full of natural light, mountain views, and stylish touches throughout. The home is situated beautifully between 2 mountains and is only a short walk from the Appalachian Trail, which is perfect for anyone who loves to hike! The bright and open living room consists of comfortable seating and a large smart TV with Roku streaming channels like Netflix, Hulu, etc (no cable channels). There are plenty of fun board games and puzzles to keep friends and family entertained. Just off of the living room is the well appointed kitchen that has brand new appliances, tons of storage, a large kitchen island with seating and lots of prep space for the home chef. Next to the kitchen is the dining room with a table that comfortably seats 10+. The large main floor master suite boasts a king size bed, smart TV with streaming channels, a queen size sleeper sofa, and an en suite bathroom with a large glass and tile walk-in shower. Just off of the living room is another bedroom with a queen size bed. There is an additional full bathroom with a tub/shower combination. Lastly, the the washer and dryer is also located on the main floor for the guest's convenience.brbrUpstairs, there are 2 more bedrooms and a full bathroom with a tub/shower combination. One bedroom has 2 queen size beds and a Roku TV, while the other has 2 bunk beds (double on the bottom and single on top) and a twin size bed. This bedroom can sleep 4 adults comfortably or 7 kids. At the top of the stairs, on the landing, there is a comfortable reading chair to soak up the sun and catch up on your latest book. brbrLower level Playroom: Guests can enjoy the newly finished basement with 2 TVs, foosball table, and ping pong! There is a Nintendo Wii with 20+ games and 6 controllers. It is the perfect hang out space for kids and parents alike looking for a fun place to unwind after a busy day sight-seeing or skiing. brbrOutside: Is a fabulous outdoor patio with lots of seating, a large fire pit, a hot tub that seats 4 to 6 people, and a propane BBQ grill. There are beautiful Mountain Views and the Appalachian Trail is only a short walk away, so you can literally walk outside your door and go for a hike. brbrLocation: This terrific location is less than 10 minutes to Great Barrington, 15 minutes to Stockbridge, and just 25 minutes to Tanglewood!

5 Stars w/ Hot Tub, Sunny Patio, Game Room, Views!

Great Barrington, Massachusetts, United States

Bed

Bath

14

Sleeps

$680.25

The Garden House, Quiet Elegance with One-Level Living, in a Park-Like Setting. Sleeps 10brAmenities: 4 bedrooms, 4 full baths + 1/2 bath, Large screened in porch, outdoor seating with grill, large lush lawn, 3 Smart TVs, chef's kitchen will high-end stainless appliances, Spectrum Wifi, Air Hockey, Playroom, AC, Garage with access for 1 car, wood-burning fireplace, 2 washer/dryer sets. No Pets (no exceptions) No Smoking.brbrThe Garden House is your perfect one-level property for guests of all ages. The living room is inviting with 2 velvet sofas, a wood-burning fireplace, a baby grand piano (available, but not a toy) and game table. Tuck into the reading nook with many engaging books, suitable for both adults and children.brbrThe Kitchen: Skylights, gas fireplace, dining area+extra seating. Kitchen has direct access to the screened porch!br- 6 burner gas range, dishwasher, and custom freezer/fridge with ice makerbr- Small appliances include: standard coffee maker, electric water kettle, air fryer, blender.br- 2 islands provide ample counter space and oodles of storagebr- Adjacent screened-in porch with many seating options and outdoor lighting.brbrBedrooms and Layout: 4 bedrooms with 4 full bathrooms are all on one level. Sleeps br- Primary has a king bed, TV, ensuite full bathroom with X-large walk-in shower.br- Guest #2 has a queen bed, ensuite with a showerbr- Guest #3 has two twin beds and its own bathroom, with a tiled tub/shower.brOn a separate wing is The Apartment with Guest #4 bedroombr- Easily accessible from the main house, just down a short hall from the living room but also has its own private entrance.brThe apartment has a living room (with queen size pull-out sofa), Smart TV and a full kitchen snack space with drinks fridge and microwave. The bedroom with a Queen bed has its own bathroom with walk-in shower and stacked laundry.brbrOther features: lower level playroom with Air Hockey, Second laundry room in the basement, a 1/2 bath near the kitchen. Please see the floor plan for better understanding!brbrOutside: 3 acres of park-like lawn lawn, privacy. There is a small stone terrace with seating and lovely mature gardens.brGarage available for 1 car.brbrLocation: Perfect and central - close to all major Berkshire venues! Easy walk to The Barn for food and live music! Less than 10 minutes to the center of Great Barrington and only 30 minutes to Tanglewood. Ski Butternut and Catamount ski are both 10 minutes drive.brNo pets, no smoking.

Fireplace, Privacy, Screen Porch, 1 Level Living!

Great Barrington, Massachusetts, United States

Bed

Bath

10

Sleeps

$661.97

Highland Amenities: 4 Bedrooms, 2.5 baths, Sleeps 10. Pet friendly with a fully fenced yard (pet fees apply), hot tub (year round) propane grill, outdoor seating w/ sun umbrella on patio + chaises for sun deck, lovely gardens, high speed internet, mini split AC, ice maker, wood stove (wood included), Smart TV, washer/dryer, games, all linens included, attached garage. Gate access to McAllister Park for hiking and swimming and close to Lake Mansfield, Butternut, GB Busking in Summer! No Smoking.

Fall Weekends: Hot Tub, Green River Hike, Sleeps 8+

Great Barrington, Massachusetts, United States

Bed

2

Bath

10

Sleeps

$640.09

Amenities Include: 3 bedrooms and 3 full bathrooms (sleeps 8 in beds), bonus finished basement game room, high speed internet/WiFi, AC throughout, 2 Smart TVs with streaming channels like Netflix & Hulu, Billiards Table/Air Hockey Table, All new stainless steel appliances, washer/dryer, 2 car garage with direct entry into the kitchen, fully fenced back yard, outdoor seating with propane BBQ grill, outdoor umbrella, seasonal fire pit, loads of fun toys and all the linens are included, too.brbrHill House Modern: a lovely mid-century modern boasting one-level living, with easy access to Lake Mansfield Park and the center of downtown Great Barrington. The house is light-filled, spotlessly clean, with thoughtful touches throughout. The front room has a cozy elegant seating area with fun battery operated candles in the fireplace for great ambience. There are books and games available and a large coffee table perfect for a puzzle or a board game. This is a great room to enjoy appetizers before dinner or to cozy up in with a book. The recently updated kitchen has all new stainless steel appliances which include: a refrigerator/freezer, electric range, dishwasher, microwave, toaster, and standard drip coffee maker. With plenty of counter space and kitchen, preparing your meals is a breeze. The kitchen is eat in with table seating for 6 along with additional counter seating for 3. The large media room is just off the kitchen and offers guests comfortable seating with it's oversized leather sofa & chairs, alongside a 65 Smart TV with access to all of your favorite streaming channels. brbrBedrooms: Head down the hall from the front room to the three (3) bedrooms and two (2) full baths. The primary bedroom has a king bed and ensuite full bathroom with walk-in shower. Guest room #2 has a queen bed and guest room #3 has two (2) full size beds. These 2 bedrooms share another bathroom #2, with a tub/shower combo.brbrLower Level: The fully finished playroom has a lot to offer: with billiards table that can convert into an air hockey table, another smart TV, sitting area, indoor basketball shoot-out game, doll house, toys, games, and more. This area is multi-purpose and also includes a craft table and other fun things to do for kids of all ages. The laundry room is also located on this lower level.brbrOutside: The backyard, fully fenced, is easily accessed through the media room. There is a crushed stone patio has a dining table and chairs, outdoor umbrella, chaise lounge and propane BBQ grill. There is also a fire pit for guests to enjoy.brThe garage is attached and provides an easy access into the kitchen and ample storage place for snow gearbrbrLocation: The house is an easy walking distance into town as well as to Lake Mansfield, with a sandy beach, swimming (lifeguard on duty in summer), picnic tables, swings, play structures, standing charcoal grills and hiking trail - all less than a 1/2 mile from the house. The center of Great Barrington is also less than a mile away and offers shops, restaurants, bars, galleries, bakeries, coffee, movies and more to explore. Both Ski Butternut and Catamount Ski are just 10 minutes away and Tanglewood is only 25 minutes. You will not want to miss this sweetly re-done and perfectly located rental opportunity, granting you access to all the Berkshires has to offer.brbrNo smokingbrPets are welcome guests, along with a pet fee. brPlease see House Rules for more details

Chic, Mid Century Modern 3 bedroom Home, Close to Downtown GB!

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Select Dates for Price

span style=font-family:Verdana,Geneva,sans-serif;Long Pond Views: New Built Contemporary with 4 bedroom, 4 full baths, sleeps 8 in beds. Amenities include access to the lake, 2 kayaks, 2 paddle boards, a main floor bedroom (with the master bedroom upstairs), a fire pit (wood included) Adirondack chairs, hammock, sun deck, Weber grill, 4 smart TVs, high speed internet and wifi, bright kitchen, washer/dryer, central AC, ping pong table, lovely water views. All linens included. Pets are considered with a $150 pet fee, per pet. No Smoking, brThis brand new construction home is light and bright with plenty of thoughtfully designed space to be able to spread out and enjoy Berkshire living, at its finest! The large and open kitchen has everything the home cook needs along with plenty of counter space and storage. A brand new state-of-the-art electric oven range was installed October, 2023 for an even better cooking experience! There is a huge island, a standard coffee maker and a Keurig coffee maker, toaster, vitamix blender, a microwave...and more. We have it nicely equipped for a guest to easily prepare and serve Thanksgiving dinner. The dining room table comfortably seats 8 guests along with 2 extra stools at the counter. The media room is just off the dining area and it has cozy seating, a Smart tv, and an area with yoga mats, a big ball and rollers for stretching and yoga. Boasting 4 bedrooms and 4 full baths, there is one main floor bedroom, with a queen bed, and three (3) other bedrooms upstairs (king, queen, and full). The main floor bedroom has a queen size bed along with a chest of drawers, closet, desk, Smart tv, and the shared bathroom is just across the hall with a walk-in shower and laundry room! There is also an office on the main floor with a desk, white board, monitor and printer - all for guests use. Please use a little and leave a little printer ink brThere are 3 more guest rooms upstairs, all good-sized, and each has its own full bathroom. The primary Guest room, with King bed, has a walk-in cedar closet and a lovely ensuite bath with large soaking tub and a walk-in shower. The third Guest room has a Queen bed, with its own ensuite bath with a walk-in shower. The 4th guest room has a Full bed and its own full bath (tub/shower combo) just across the hall.brJust off the dining area, sliding doors open onto the large patio and yard with views of the lake. There are plenty of comfy seating along with Adirondack chairs to relax in, a hammock, propane BBQ grill and a solo fire-pit, wood included. Take a short walk down to the water where you can swim, kayak, paddle board, or simply sit and enjoy nature. Round Pond is located right next to Long Pond and the 2 are often confused. This home has access to Round Pond, which is the larger of the 2, at 54 acres. (Speed boats are not permitted only trolling/electric motors.)brThe location of this home can't be beat - It's under 10 minutes to the center of Great Barrington, 15 minutes to Butternut, and 20 minutes to Tanglewood!

Newly Built 4 Bedroom Lake House with Kayaks & Paddle Boards!

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$491.67

Amenities: 3 bedrooms, 1.5 baths, (sleeps 6 in beds or 8 Max.) WIFI, AC, SmartTVs with Spectrum cable, local phone, good cell service available, side deck with outdoor seating and grill, washer/dryer, walk-to Lake Mansfield and easy walk to the center of Great Barrington! NO SmokingbrbrCastle Townhouse is a delightful new listing, completely renovated, and in a wonderful central location - just steps to the center of Great Barrington and a few minutes walk to lovely Lake Mansfield! The portico welcomes you into the front foyer from the wrap-around front/side porch with outdoor seating. Just inside, there is a large main closet perfect for all of your Berkshire gear. The main floor is tidy with a sumptuous living room, complete with a new flat screen SmartTV, and very cozy seating. The kitchen is perfection with all new stainless appliances, a small wall-mounted TV, counter seating for 2, a huge island for prepping and a country style table that seats 6+. There is a darling small deck area off the kitchen door, which houses a gas grill during the warmer months.brUpstairs, you will find all 3 bedrooms: the master bedroom with queen bed, and two guest bedrooms -- one with a queen bed, the other with double (extra wide!) bunk beds. This third bedroom could sleep 2 adults, 2 kids (or even 4 smaller kids)... or a grandparent who wants to bunk in with small ones - there are many possibilities! These three bedrooms share a very large tiled full bathroom with a tub/shower combination, along with a large stacked washer and dryer. There is a 1/2 bath on the ground floor as well.brOutside, you have the wrap-around porch with seating, and the kitchen deck with a grill. There is room for two cars with off-street parking in the summer, and room for one car during the winter holiday periods. The Mahaiwe Performing Arts Center, Castle Street Cafe, and all of downtown Great Barrington is just a few minutes' walk from your door. This is truly a marvelous location!

Pristine 3 Bedroom, Walk-to Gt Barrington Center!

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$414.13

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.

Twin Maple Farm: Charming Modern Farmhouse

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$2047.83

Welcome to Moose Lodge – A 7,500 Sq. Ft. Berkshires Luxury RetreatbrbrExperience the pinnacle of comfort and entertainment at Moose Lodge, a stunning 7,500 sq. ft. retreat nestled in the heart of the Berkshires. Perfect for gathering with friends and family, this expansive property offers an abundance of space, luxurious amenities, and a secluded location while keeping you close to vibrant local communities and attractions.brbrWhy You’ll Love Moose Lodge:brExpansive Living Space: Spread out and relax in 7,500 sq. ft. of thoughtfully designed interiors, perfect for both quiet moments and lively gatherings.brFully Appointed Outdoor Cooking Area: A chef’s dream with everything you need to prepare and enjoy meals al fresco.brEntertainment for Everyone:brHome Theater: A state-of-the-art space for cozy movie nights.brGame Room: Enjoy a billiards table, foosball, poker table, and blackjack table—perfect for hours of fun and friendly competition.brLuxurious Bedrooms: Rest and recharge in plush, comfortable accommodations with serene views.brOutdoor Bliss: Relax on the spacious patio, take in the fresh air, and enjoy evenings by the fire pit under the stars.brThe Perfect Berkshires Location:brNature’s Playground: Explore nearby hiking trails, lakes, and scenic drives, all just steps away from Moose Lodge.brCultural Gems: Minutes from charming towns with farm-to-table dining, boutique shops, and iconic attractions like Tanglewood and the Norman Rockwell Museum.brWith its sprawling 7,500 sq. ft. layout, Moose Lodge is ideal for creating unforgettable memories. Whether you’re enjoying a movie in the theater, competing in the game room, or dining under the stars, this luxurious retreat has everything you need for the perfect escape.brbrBook your stay at Moose Lodge today and let the adventure begin!

Lodge

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

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$831.45

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.

The Summerwood Hideout | Mins to Downtown! • Pool

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$539.51

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

$469.14

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.

Minutes from downtown Great Barrington, Convenient location

Great Barrington, Massachusetts, United States

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Bath