House holiday rentals in Sheffield

4.97 out of 5 average rating, 177 reviews

A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.

Home in Catskill

Cheerful Catskill Village Cottage

Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

4.89 out of 5 average rating, 134 reviews

A two-story house is set amidst greenery, featuring a fenced yard with varied foliage. A spacious deck equipped with a red umbrella is visible. A sunken fire pit is highlighted in the garden area, surrounded by trees and bordered by a quiet road.

Home in Craryville

The Gatehouse at Raspberry Ridge

Quiet, private house for a country get-away. Renovated 2 bedroom, 1 bath home can sleep up to 2 couples. Gated and fenced yard offers privacy and security for children or dogs. Enjoy a spacious deck and sunken fire pit for outdoor dining or lounging. Bedrooms and living space upstairs are bright, airy with cozy wood stove for cool evenings. Kitchen is well-stocked; has a dishwasher. Laundry facilities downstairs; entertainment room with large screen TV and pull out couch. WiFi available.

A hot tub sits on a polished wooden deck, surrounded by greenery. Soft lighting from string lights illuminates the area. A colorful striped pillow rests on a lounge chair, with a patterned plate and drink placed nearby, creating a relaxing outdoor retreat.

4.94 out of 5 average rating, 125 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

10 MINUTES TO CATAMOUNT Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 7 minutes to downtown Great Barrington, this stylish, cozy rental has everything you need for a great getaway. A new renovation brings modern amenities to this classic 50’s cottage. Enjoy a chef’s kitchen, 500 sq-foot deck with hot tub, and thoughtful touches like yoga mats, a record player, board games, and a backyard hammock. Monthly ski rental discounts are available!

4.94 out of 5 average rating, 145 reviews

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

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.

4.99 out of 5 average rating, 137 reviews

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

4.84 out of 5 average rating, 157 reviews

A cozy living area features two dark gray sofas adorned with decorative pillows, arranged around a light-colored coffee table. Natural light enters through nearby windows, and artwork depicting serene outdoor scenes is displayed on the walls. A mini-split air conditioning unit is mounted above for comfort.

Home in Craryville

Copake Lake Cottage Near Hiking and Waterfalls

Renovated, art-filled cottage just 500 ft from Copake Lake. This 2 bedroom 1 bathroom house is also close to hiking trails, waterfalls, apple picking, & a winery in the fall, and in winter, there’s skiing at Catamount, and a distillery nearby. A house for all seasons! Please note the house is 5 houses back and across a quiet road from the lake, and the dock is in the lake from the beginning of May to mid-September. But there is plenty to do up here during the rest of the year!

A light-filled bedroom features a white bed with plush bedding, complemented by two windows covered with dark blinds. A small nightstand holds a lamp, and a wooden chair adds to the decor. The walls are adorned with framed photographs.

4.95 out of 5 average rating, 105 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!

A charming two-story home is set on a landscaped plot with a gravel driveway. A wooden staircase leads to the entry, flanked by vibrant flower beds. The natural backdrop features lush trees and a striking granite ledge, creating a peaceful and inviting outdoor environment.

4.99 out of 5 average rating, 135 reviews

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.

A serene bedroom is presented with a spacious bed adorned with soft linens and a cozy throw. Two bedside tables hold elegant lamps, and natural light floods the room through large windows. A decorative wreath hangs above the headboard, enhancing the tranquil ambiance.

4.99 out of 5 average rating, 119 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, 298 reviews

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

4.96 out of 5 average rating, 276 reviews

The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.

Home in Monterey

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

4.98 out of 5 average rating, 102 reviews

A spacious living area features a large, cushioned sectional sofa in a warm hue, complemented by a round coffee table. Natural light floods through tall windows, highlighting a minimalistic bookshelf and a stylish armchair in the corner, enhancing the room's cozy atmosphere.

Home in Hudson

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

Popular amenities for house rentals in Sheffield

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 5 reviews

Poolside Woodlawn Getaway

4.96 out of 5 average rating, 167 reviews

A spacious cedar hot tub sits peacefully outdoors, surrounded by a natural setting of trees and open space. Bubbles rise from the water, creating a relaxing atmosphere. Clear blue skies are visible above, enhancing the tranquil environment.

Home in Hudson

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4.98 out of 5 average rating, 102 reviews

The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.

Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

A bright living room is highlighted by a grand piano and a modern gas fireplace, both set against a light brick wall. Large windows provide natural light, and wooden flooring adds warmth. A comfortable dark sofa and armchairs are arranged around a glass coffee table.

4.99 out of 5 average rating, 81 reviews

Stunning luxury home with pool

Superhost

A contemporary living area is illuminated by natural light, featuring a modern wood-burning stove and large glass doors that lead to a tranquil outdoor space. The minimalist design includes a cozy sofa, a stylish chair, and a simple desk, with views of lush greenery outside.

Home in Hillsdale

4.89 out of 5 average rating, 37 reviews

Hilltop: Panoramic Views w/ Pool near Catamount

5 out of 5 average rating, 106 reviews

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

5 out of 5 average rating, 20 reviews

The exterior of the home is showcased, revealing a charming blend of rustic wooden shingles and modern design. Large windows and a stylish doorway invite natural light, while a stone foundation adds character. Lush grassy areas surround the house, enhancing its serene setting.

Home in East Chatham

Stylish Rural Sanctuary! (+ Summer Pool)

A sunlit backyard features a heated inground pool surrounded by a paved patio. Lounge chairs are positioned near the water, and shaded seating areas are provided by umbrella-covered tables. Lush green trees and manicured grass create a serene outdoor setting.

4.93 out of 5 average rating, 30 reviews

Peaceful and Private Setting

Weekly house rentals

A modern eat-in kitchen is highlighted by wooden beams and a rustic kitchen island. Wooden cabinetry complements the black appliances, while natural light pours in through sliding glass doors. A gray rug enhances the space, creating a functional and welcoming atmosphere.

4.84 out of 5 average rating, 32 reviews

Cozy Cottage Route 7 Sheffield

The image captures a vibrant garden filled with blooming flowers in various shades. A grassy area leads to a rustic red house nestled among trees, providing a serene and inviting environment. Several large bushes contribute to the lush greenery surrounding the property.

4.97 out of 5 average rating, 39 reviews

Bull Hill Bungalow

4.99 out of 5 average rating, 75 reviews

A spacious living area is illuminated by natural light, featuring large windows that offer views of the surrounding trees. Comfortable seating options include a sectional sofa and two round ottomans. A modern dining table for six complements the open layout, creating an inviting atmosphere.

Home in Salisbury

Curated Contemporary for lakes, forest & ski hills

A charming house is nestled among autumn foliage, displaying warm earthy tones. A winding stone pathway leads to the entrance, framed by a well-maintained stone wall and lush greenery. Colorful leaves adorn the surrounding trees, creating a serene and inviting landscape.

5 out of 5 average rating, 17 reviews

Seekonk Hill

The historic house is set against a backdrop of rolling mountains, surrounded by lush greenery and flower gardens. A tranquil lawn stretches before the home, which features large windows and a welcoming front porch, inviting guests to explore the expansive property.

4.97 out of 5 average rating, 38 reviews

Private Berkshires Estate w/ Tennis Court

The exterior of a transformed church features a pointed steeple and a central double door framed by a decorative arch. Stained-glass windows are visible, adding a historic charm against the dark wood siding. The surrounding area is lined with trees, hinting at the serene natural setting.

5 out of 5 average rating, 20 reviews

Berkshires Black Abbey

Superhost

An aerial view of a private home nestled among vibrant trees that showcase fall colors. The house features a light exterior with a spacious lawn, surrounded by a field and dense foliage, offering a peaceful retreat in nature.

4.84 out of 5 average rating, 25 reviews

Whitney by AvantStay | Private Berkshires Estate

The living room features a bright and airy design with large windows that provide natural light. A soft sectional sofa offers ample seating, facing a cozy fireplace surrounded by stone. Decorative art pieces and a wooden ceiling enhance the room's warmth and character.

5 out of 5 average rating, 27 reviews

Hilltop Ski and Sun Chalet with Hot Tub

Private house rentals

A spacious bedroom features a large bed adorned with white linens and decorative pillows. A warm fire crackles in a brick fireplace, complemented by wooden beams overhead. Soft lighting is provided by two bedside lamps, and a colorful area rug adds a touch of vibrancy to the room.

4.89 out of 5 average rating, 44 reviews

Cozy. Clean. Free bagel shop.

A spacious living area showcases a large blue sectional sofa surrounding a low coffee table atop a decorative rug. Large windows allow natural light to fill the space, while a cozy decorative fireplace adds warmth. The open layout connects to the dining area in the background.

4.97 out of 5 average rating, 29 reviews

Perfect Nature Retreat In Great Barrington

4.92 out of 5 average rating, 76 reviews

A welcoming entryway features a vibrant yellow door framed by light fixtures, complemented by a decorative bear sculpture on a stone pathway. A large bush and windows add greenery to the red exterior of the house, creating a homey appearance.

Home in Copake

Yellow Door House

Superhost

A cozy living room features a light grey sofa adorned with patterned cushions. A wooden trunk serves as a coffee table in front of the sofa. Natural light filters through a skylight, highlighting the warm red walls and floral arrangement on a side table.

Home in Norfolk

4.86 out of 5 average rating, 7 reviews

entire farm style house

An expansive sun deck features a large dining table with white chairs, sheltered under a sizable umbrella. Comfortable seating arrangements are also present, providing a relaxing area that overlooks the lush greenery of the surrounding trees.

4.85 out of 5 average rating, 13 reviews

Deck, River Views, Mini Gym, Sleeps 8

5 out of 5 average rating, 40 reviews

A spacious outdoor seating area is highlighted with a large yellow umbrella, providing shade over comfortable seating arranged on a stone patio. A serene waterfront view is visible in the background, framed by lush greenery and trees.

Home in Sandisfield

Waterfront oasis in heart of Berkshires

A spacious living area features high ceilings with wooden beams and several large windows, allowing natural light to fill the space. A modern sofa is arranged around a stylish coffee table, with a cozy rug underfoot. A fireplace adds warmth, and contemporary artwork adorns the walls.

4.93 out of 5 average rating, 94 reviews

House Among Trees - A Perfect Holiday Getaway