
Holiday rentals in Sheffield
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Top-rated holiday rentals in Sheffield
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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!

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.

Modern Farm House 5 minutes from Great Barrington
Completely updated with style, this shingled farmhouse combines modern decor with the charm of a country home. Enjoy a spacious, sunny kitchen that connects to a large outdoor patio featuring a fireplace. The cozy living room has a large flat-screen TV for streaming. The first floor includes a bedroom with an attached bathroom & laundry. The second floor suite boasts cathedral ceilings a luxurious jet-powered shower. This home offers a perfect blend of comfort and elegance for your stay!

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.

Stay in Downtown Canaan
This light-filled space with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. WELL BEHAVED dogs are welcome. Poop bags are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK to see what our area offers!!!

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.

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

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!

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.

The Cottage at The Barrington House
Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

Artist Cottage
Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.
Popular amenities for Sheffield holiday rentals
Other great holiday rentals in Sheffield

Beautiful Berkshires Farmhouse | Ski & Explore

Pennybrook Cottage: A Design-Lover's CT Retreat

Yellow Door House

Seekonk Hill

Modern Dairy Barn

The Nest 5 min walk to downtown Great Barrington

Charming Handcrafted Cottage in the Berkshires!

Whitney by AvantStay | Private Berkshires Estate
When is the best time to visit Sheffield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹20,517 | ₹20,517 | ₹18,157 | ₹18,157 | ₹18,157 | ₹24,058 | ₹25,874 | ₹25,420 | ₹20,699 | ₹22,242 | ₹24,693 | ₹26,781 |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Sheffield?
Four-legged friends are welcome in Sheffield. Choose from more than 30 vacation rentals for guests traveling with pets.
Do house rentals in Sheffield have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Sheffield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Sheffield?
Experience the best of Sheffield with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Sheffield have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Sheffield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Sheffield?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with free parking, over 40 homes with air conditioning, over 50 homes with wifi, over 50 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Sheffield?
Sheffield has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Sheffield?
Yes! Work meets play with ease at over 50 vacation rentals in Sheffield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Sheffield have wifi?
Absolutely! We offer over 50 house rentals with wifi in Sheffield. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Sheffield

Total holiday rentals
Explore 90 holiday rentals in Sheffield

Nightly prices starting at
Sheffield holiday rentals start at ₹8,171 per night before taxes and fees

Verified guest reviews
Over 4,720 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
90 of Sheffield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Sheffield rentals

4.9 Average rating
Sheffield stays are highly rated by guests – averaging 4.9 out of 5!
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- Hunter Mountain
- Six Flags New England
- Thunder Ridge Ski Area
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Windham Mountain
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Mount Southington Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Ski Sundown
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Benmarl Winery
- Poets' Walk Park




