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House holiday rentals in Sheffield

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Quick stats about house rentals in Sheffield

  • Total holiday rentals

    Explore 50 holiday rentals in Sheffield

  • Nightly prices starting at

    Sheffield holiday rentals start at £103 per night before taxes and fees

  • Verified guest reviews

    Over 1,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Sheffield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sheffield rentals

  • 5 Average rating

    Sheffield stays are highly rated by guests – averaging 5 out of 5!

Top-rated house rentals in Sheffield

Guests agree: these houses are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of a colonial house is framed by lush greenery and towering trees. The white siding is complemented by black shutters, and a welcoming entryway is visible. Sunlight filters through the branches, casting gentle shadows on the well-manicured lawn.
Home in Great Barrington

Stylish colonial, 4 acres, 9 min Gt Barrington

Enjoy a beautiful, modern-furnished colonial house situated on 4 private acres, built in 1800 & updated for maximum comfort. Easy driving to Tanglewood, Jacob's Pillow, Ski Butternut, Kripalu and many fantastic dining options. Open kitchen/living room with cathedral ceilings, 4 bedrooms with views of spacious property and surrounding farmland. Full kitchen, dishwasher, woodburning stove, 2 bathrooms, laundry, wifi. Minimally and stylishly furnished, with space for couples, families & friends.

4.91 out of 5 average rating, 101 reviews
Top guest favourite
A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.
Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

4.99 out of 5 average rating, 250 reviews
Guest favourite
A spacious living room features a large U-shaped leather couch and a central ottoman, offering seating for several guests. Natural light pours through multiple windows, highlighting the wooden walls and stone accents. The kitchen area is visible in the background, enhancing the open layout.
Home in Great Barrington

Great Barrington, Cabin Sleeps 14, Walk To Town

You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 350 feet walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more! Short walk to a great lake with a beach area - bring your dogs and family to swim in or walk around and enjoy the nature reservation!

4.85 out of 5 average rating, 138 reviews
Top guest favourite
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.
Home in Great Barrington

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.

4.94 out of 5 average rating, 145 reviews
Top guest favourite
A newly remodeled kitchen showcases white cabinets complemented by a marble countertop and a decorative backsplash. A rustic wooden dining table with chairs is positioned near a window, while a vibrant area rug adds warmth to the space. Modern appliances are neatly integrated into the design.
Home in Salisbury

Under Mountain House

Our home is designed to be your home away from home! It has been newly renovated with comfort in mind so you can enjoy your stay in the Berkshires. Whether you are here to hike parts of the Appalachian Trail, stroll into town for a leisurely meal, enjoy Lime Rock Race Track or explore the many surrounding New England towns you can be assured you will always have a comfortable home to come back to!! My home is located just a 3 minute walk to the center of town and the historic White Hart.

4.98 out of 5 average rating, 180 reviews
Guest favourite
A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.
Home in Sheffield

Perfect Peaceful Berkshire Location !

We have two rentals. Only one rental is rented at a time. This rental has 2 bedrooms, a fully equipped kitchen and is super clean. (THE 1 BEDROOM LISTING is called “Great Berkshire Getaway”) Conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit

4.92 out of 5 average rating, 130 reviews
Top guest favourite
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.
Home in Sheffield

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, 133 reviews
Top guest favourite
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.

4.96 out of 5 average rating, 309 reviews
Top guest favourite
Home in Sheffield

Berkshire Getaway~ No Pet Fee! Walk to Distillery

Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within steps of Big Elm Brewery & Berkshire Mountain Distillery. Peloton included. Pet-Friendly. Minutes to great hiking, skiing, antiquing & more Seasonal Hot Tub is not available until further notice, sorry for the inconvenience.

4.9 out of 5 average rating, 100 reviews
Top guest favourite
The charming farmhouse features a covered porch with seating, surrounded by a vibrant garden filled with colorful flowers. Solar panels are visible on the roof, while a grassy area and a small fire pit enhance the outdoor space, inviting relaxation in a natural setting.
Home in Great Barrington

Walk to Town! Great Barrington 4-bedroom farmhouse

Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

5.0 out of 5 average rating, 116 reviews
Top guest favourite
The exterior of a spacious house is shown, featuring a light-colored facade and a neatly landscaped yard. A winding pathway leads to the entrance, surrounded by lush greenery and colorful flowers. A large window reflects the natural light filtering through the trees.
Home in Millerton

The House in a Beautiful Small Upstate Town

This is a house to enjoy with the family with a lot of space and many activities, in a small town but with a lot of tourism. You can visit the town which it has a small cinema, and Rail trail for walking or biking, and it has many restaurants nearby. This house includes a living room, kitchen, 4 bedrooms, 3 full bathrooms, deck, and a big backyard. You can also do BBQ s outside.

4.97 out of 5 average rating, 263 reviews
Top guest favourite
A charming home is set on a raised stone foundation, featuring a bright blue front door that adds a pop of color. Lush green grass surrounds the property, complemented by a stone walkway leading to the entrance. Mature trees and yellow forsythia bushes provide a natural backdrop.
Home in Great Barrington

The Hideaway: Berkshire Home - village of Egremont

**NEW KITCHEN APRIL 2025!!**. Welcome to our family's home in the village of Egremont (part of Great Barrington). Both the house and property are open and inviting! You'll feel relaxed the minute you arrive. The kitchen is equipped with everything you should need for your stay. Our house is perfect for just a couple or a group. Please reach out to me with any questions!

4.95 out of 5 average rating, 147 reviews

Popular amenities for house rentals in Sheffield

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

4.88 out of 5 average rating, 220 reviews
Top guest favourite
Home in Athens

Lake House close to Skiing & Indoor Hot Tub

4.96 out of 5 average rating, 112 reviews
Top guest favourite
A spacious white cottage is set against a vibrant green lawn, framed by blooming white flowers. Expansive trees surround the property, overlooking rolling hills that stretch towards a tranquil river in the distance under a clear blue sky.
Home in Coxsackie

Hudson River estate guest cottage

4.98 out of 5 average rating, 108 reviews
Top guest favourite
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

4.98 out of 5 average rating, 134 reviews
Guest favourite
Home in Hudson

Hudson River Sunset Getaway

4.92 out of 5 average rating, 111 reviews
Guest favourite
A spacious living area features a large sectional sofa with dark cushions, complemented by a wooden chair with patterned fabric. A modern ceiling fan hangs above, and a sleek fireplace is positioned nearby. Large windows invite natural light, providing a view of the greenery outside.
Home in Hudson

Casa Luna Country Retreat with Pool, Hudson, NY

4.92 out of 5 average rating, 266 reviews
Top guest favourite
A two-story house stands on a gently sloping hill, surrounded by lush green grass. The property features a large, covered porch that wraps around part of the home, offering views of the expansive yard and surrounding trees.
Home in Tivoli

Upstate Getaway btw Rhinebeck+Hudson

4.98 out of 5 average rating, 102 reviews
Top guest favourite
Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.
Home in Athens

Private lakefront home, hot tub & resort amenities

4.95 out of 5 average rating, 192 reviews

Weekly house rentals

Guest favourite
A light-colored house sits amid lush greenery, surrounded by trees and a manicured lawn. The building features a simple architectural style with a peaked roof and a welcoming porch, offering a serene view of the natural landscape.
Home in Sheffield

Serene Berkshire Artist's House

4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Sheffield

Family friendly house with fenced yard & fire pit

4.97 out of 5 average rating, 29 reviews
Guest favourite
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.
Home in Sheffield

Bull Hill Bungalow

4.98 out of 5 average rating, 55 reviews
Top guest favourite
The exterior of a charming house is illuminated by soft outdoor lighting at dusk. A darkening sky transitions from blue to deeper hues, while snow blankets the ground. The structure features a clean design, with large windows visible, providing a glimpse of a warm interior.
Home in Sheffield

The Kellogg House in the Heart of The Berkshires

4.99 out of 5 average rating, 72 reviews
Top guest favourite
Home in Sheffield

All new mountain retreat near Great Barrington.

5.0 out of 5 average rating, 9 reviews
Superhost
Home in Sheffield

Whitney by AvantStay | Private Berkshires Estate

4.83 out of 5 average rating, 35 reviews
Top guest favourite
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.
Home in Great Barrington

Berkshires Black Abbey

5.0 out of 5 average rating, 46 reviews
Top guest favourite
A spacious home is framed by lush green grass and trees, with colorful autumn foliage in the background. A welcoming front porch with steps leads to the entrance, under a partly cloudy blue sky.
Home in Sheffield

Beautiful Berkshires Home | Perfect For 3 Families

4.97 out of 5 average rating, 29 reviews

Private house rentals

Guest favourite
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.
Home in Great Barrington

Hilltop Ski and Sun Chalet with Hot Tub

4.97 out of 5 average rating, 61 reviews
Superhost
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.
Home in Sheffield

Cozy Cottage Route 7 Sheffield

4.82 out of 5 average rating, 49 reviews
Top guest favourite
A cozy living area features a light-colored sofa and two armchairs facing a simple black side table. A gas fireplace is centered against a white wall, while large windows allow natural light to flow in, highlighting the wood-paneled ceiling.
Home in New Marlborough

Scenic Berkshire retreat near Great Barrington

5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Great Barrington

Lovely house in the Berkshires

4.87 out of 5 average rating, 31 reviews
Top guest favourite
A spacious living room features a cozy leather sofa and a soft gray area rug, providing a comfortable environment. Natural light floods in through multiple windows, while a gas fireplace adds warmth. A dining area with sleek chairs is visible in the background.
Home in Sheffield

Charming Country House with a Hot Tub

4.93 out of 5 average rating, 46 reviews
Top guest favourite
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.
Home in Great Barrington

Seekonk Hill

4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Great Barrington

A Berkshires Abode - Minutes to Ski & Downtown GB!

4.97 out of 5 average rating, 31 reviews
Top guest favourite
A modern kitchen is showcased with white cabinetry and marble countertops. A central island with bar stools holds a bowl of fresh fruit. Large windows provide natural light, while stainless steel appliances and potted plants add to the inviting atmosphere.
Home in Great Barrington

Walt's Townhouse - Berkshire living at its best

5.0 out of 5 average rating, 86 reviews

When is the best time to visit Sheffield?

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Avg. price£244£297£240£247£235£261£244£232£221£228£243£268
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Destinations to explore