Holiday rentals in Sheffield

4.99 out of 5 average rating, 331 reviews

Loft in Great Barrington

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

4.94 out of 5 average rating, 416 reviews

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

4.91 out of 5 average rating, 331 reviews

Flat in Copake Falls

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!

4.98 out of 5 average rating, 103 reviews

Guest house in Millerton

Loft in the Pines

Loft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY & Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking & skiing. Easy walk to antique shops & delicious restaurants or put your feet up and relax! 1.5 baths, living room with flat screen TV, dining room & fully equipped kitchen & expansive deck to take in the view. Rent with House in The Pines for a larger group

4.94 out of 5 average rating, 154 reviews

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

4.88 out of 5 average rating, 104 reviews

Flat in Great Barrington

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"Tv with Hulu Live

4.99 out of 5 average rating, 143 reviews

Flat in Canaan

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

5 out of 5 average rating, 364 reviews

Flat in Sheffield

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

4.95 out of 5 average rating, 100 reviews

Great Berkshire Getaway !

"238 Main" has two rentals. Only one rental is rented at a time. Rental #2 has a Queen size bed, FULLY EQUIPPED KITCHEN and is SUPER CLEAN! (SEE THE TWO BEDROOM LISTING #1) We are conveniently located between Butternut and Catamount ski stations. Fully renovated with private garden, entrance, terrace and parking. Queen size bed. Hi Speed Wifi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hair dryer and toiletries. In the heart of the Berkshires! Come visit!

4.99 out of 5 average rating, 121 reviews

Home in Great Barrington

Granite Ledge, Modern home in a unique setting

Welcome to Great Barrington, the heartbeat of the Berkshires! This newly remodeled home that sits on 3.5 acres, is conveniently located 1 min from Butternutt Ski Mountain, and a 6 min drive from downtown main street Great Barrington. Convenient to restaurants, shops, farmers markets, art galleries, Tanglewood, Stockbridge, The Norman Rockwell Museum, Simon’s Rock, etc. Enjoy a vibrantly diverse restaurant scene and cultural events while still staying in a private setting.

4.99 out of 5 average rating, 108 reviews

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

4.99 out of 5 average rating, 311 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

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Other great holiday rentals in Sheffield

Guest suite in Canaan

4.98 out of 5 average rating, 346 reviews

Walk to Brewery in Historic Railroad Depot

SherriRating, 5 starstoday

The placed was very comfortable and cozy. Very responsive host and easy access to town. Clean and Kathryn paid attention to small amenities. Close to hiking, concerts, golfing and boating.

4.8 out of 5 average rating, 25 reviews

Cozy Cottage Route 7 Sheffield

MichaelRating, 5 stars3 weeks ago

One week stay in this very charming and well equipped home, kitchen and bath. extremely cozy. when the weather was nice the back deck was great for coffee spot. highway road noise on the front was noticeable during the day. only minor complaint was that the mattress was sagging in the middle.

Cabin in Monterey

4.87 out of 5 average rating, 235 reviews

Secluded cabin with babbling brook

CoriRating, 5 stars3 weeks ago

Truly a magical spot. We’ve stayed at many unique Airbnbs, and this one is up there as a favorite. It’s so peaceful and beautiful; the walk down makes it feel like you are truly remote and alone. The screened porch is perfect for listing to the stream at all points of the day. The cabin itself is furnished in a quirky and cozy way, and the beds are very comfortable. The full kitchen had everything needed. The host was super friendly and responsive. We would absolutely would recommend to others!

4.92 out of 5 average rating, 86 reviews

House Among Trees - A Perfect Holiday Getaway

ChristineRating, 5 stars2 weeks ago

Stayed here with some bike club friends for our annual cycling retreat in the Berkshires. Check-in and -out were super smooth; place was exactly as described, and very quiet! Amenities were very convenient and the area is beautiful. The sauna was very clean and a great treat! Grill was usable and everything we needed was available to help clean up. We would definitely stay here again! Many thanks to Swagata and Agassi for a lovely stay.

Flat in Sheffield

4.86 out of 5 average rating, 7 reviews

Historic Kellogg House Apartments - Upstairs

DanRating, 5 stars7 months ago

This is an absolutely lovely Airbnb in a scenic, peaceful, location with very, very friendly and responsive hosts. The apartment has been completely renovated, everything looks totally brand new, and the workmanship is superb. As a fellow host, I completely approve! The furnishings, linens, and other decor are what you would expect to see in a high-end hotel suite, everything extremely comfortable and spectacularly clean. When you look out the huge windows, you see a beautiful rural scene of empty fields and hills beyond, it is extremely restful and you can also sit on your own private upstairs deck. The kitchen is small, but completely adequate to cook most things you want unless you’re planning a large feast . I completely enjoyed my stay, and believe me this is really honest when I say it! One of the nicest Airbnb apartments I have stayed at.

4.97 out of 5 average rating, 29 reviews

Private Berkshires Estate w/ Tennis Court

TimothyRating, 5 stars3 months ago

The property was exactly as described and truly magical. Jill's communication was excellent and she provided an extensive PDF detailing everything about the house from AV equipment to heating and kitchen supplies. A multi-page list of surrounding restaurants, stores and attractions was also very handy. The kitchen was well-stocked with cooking supplies and the bathrooms were all clean, functioning well, and also well supplied with towels and disposables. There was an amazing collection of board games, books, and even a hidden playroom for the kids. About a 15 minute drive to catamount if you are skiing and to a huge bBig Y if you need to stock up on groceries. Will definitely come back in the spring to utilize the hiking trails and extensive gardens on property.