Pet-friendly holiday rentals in Berkshire County

Nerd Preservation Sanctuary

Nerdscapist, geekmantic country home; perfect for oddballs who wish for a crafty, private, hilarious country retreat. Featuring a bad art print collection from the glorious MA Museum of Bad Art (Or Mass MOBA). Original bad art and sculpture. Much scope for the imagination's doofiest crevices. Redonkulously close to all the local fun: tiny drive to 5 lakes, Jacob's Pillow, Tanglewood 17 mi, Otis ski, 1/2 hr to Butternut Ski & Tubing Pittsfield & Great Barrington, hour to Berkshire E & Mass MOCA.

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

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.

Cozy Berkshires Cottage

Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

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.

Kitchenette|King Bed|Couch

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 *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58" Smart TV

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

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.

Cozy Guesthouse Near Downtown, Lee

Welcome and enjoy our renovated Guesthouse at Lee, MA, staying on main street (15 minutes from Great Barrington and 20 minutes from Pittsfield). It is also 3 mins to Outlet and 19 mins to the closest Ski area.The master bedroom has a queen size soft mattress, and the second bedroom has a queen bed also. The kitchen has a brand new refrigerator, a gas range, and units for cooking. You will enjoy the comfortable stay! Owners live upstairs and be friendly to all visits.

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.