Pet-friendly holiday rentals in Great Barrington

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Best of the Berkshires + Hot Tub by Evergreen Home

Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub. Enjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

King Bed |Wi-Fi| 2m to Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *58" TV w/ Hulu + Live

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

Blackberry Cottage

Enjoy our peaceful (pet friendly) home, just a short drive to the center of Norfolk. Great for friends and/or family visits. Board games, puzzles and books inside for all; fire pit outside. Front & side decks, are perfect for relaxing. Access great cafes, shops & cultural delights in Norfolk. The nearby Ellen Battell Stoeckel Estate hosts Yale's Summer Chamber Music Concert series. It’s a home, not a hotel. I think you’ll love it!

Lake House in the Berkshire (Access Dock & Canoe

Unwind and reset at a newly built house on Lake Buel. With access to a private community dock and provided canoe, you can take advantage of life on the water. Inside this newly built house, you will find brand new furnishings and newly updated features to make your stay comfortable. Just a quick five minute drive to Great Barrington, home to some of the best restaurants that the Berkshires have to offer.

Private Home in The Berkshires (New Hot Tub!)

Leave your worries and stress behind and enjoy all the beautiful Berkshires have to offer! This fully remodeled home is ready to serve as your new favorite vacation spot! Whether you’re looking to enjoy a laid back getaway or an adventurous stay, look no further. You’re a short 10 minute drive to Ski Butternut, less than 15 minutes to Catamount, and about 20 minutes away from Tanglewood Music Center!