Hotels in Sheffield

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Tonight
Oct 27 - Oct 28
Tomorrow
Oct 28 - Oct 29
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Where to stay in Sheffield?

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,235 reviews)
The price is $95
$128 total
includes taxes & fees
Nov 25 - Nov 26
Berkshire Mountain Lodge
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

2. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,054 reviews)
Nestled in Lenox, this lodge offers easy access to Kennedy Park and Pleasant Valley Wilderness Sanctuary. The Club Room serves American cuisine, while the terrace provides a perfect spot to unwind after exploring local attractions.
The price is $133
$149 total
includes taxes & fees
Nov 3 - Nov 4
Berkshires Untold
A house with a stone patio and wooden stools.

3. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (150 reviews)
Escape to this mountain lodge near Catamount Ski Area, featuring a seasonal outdoor pool and relaxing sauna. After alpine adventures, savor complimentary breakfast before unwinding at the bar. Free WiFi and parking round out this Copake Falls retreat.
The price is $152
$170 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
Two Adirondack chairs facing a river with a forested hill in the background.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
The price is $106
$118 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A wooden boat on calm water with a house in the background.

5. Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
10.0 out of 10, Exceptional, (48 reviews)
Scenic Berkshires escape featuring an outdoor pool and rejuvenating sauna. Enjoy local flavors at The Cliff House restaurant after exploring nearby Catamount attractions. Free WiFi and parking make this wooded sanctuary even more appealing.
The price is $284
$350 total
includes taxes & fees
Nov 11 - Nov 12
Prospect Berkshires
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

6. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,008 reviews)
This peaceful hotel offers complimentary breakfast, WiFi, and parking, with Mahaiwe Performing Arts Center just moments away. Fitness enthusiasts will appreciate the on-site gym and outdoor activities, while the helpful staff ensures a comfortable stay.
The price is $75
$84 total
includes taxes & fees
Nov 22 - Nov 23
Quality Inn Great Barrington
A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

7. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
The price is $179
$250 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
Interior detail

8. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
Escape to the Berkshires in this inviting Sheffield accommodation with complimentary WiFi and parking. Start your day with cooked-to-order weekend breakfast before exploring nearby Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary.
The price is $164
$183 total
includes taxes & fees
Oct 28 - Oct 29
Wilder House Berkshires
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

9. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,007 reviews)
Nestled in South Lee, this family-friendly retreat features 4 pools total - 2 indoor and 2 outdoor, including a seasonal option. Enjoy refreshments at the pool bar or coffee shop after exploring nearby Tanglewood Music Center and Berkshire attractions.
The price is $117
$150 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

10. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (845 reviews)
Refresh in the indoor pool at this welcoming Great Barrington hotel. The fitness center adds value to each stay, while free breakfast fuels adventures to nearby Lake Mansfield Park and Housatonic River. Guests rave about the clean rooms and helpful staff.
The price is $90
$101 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

11. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (289 reviews)
Experience tranquil moments at this countryside retreat near Undermountain Golf Course and Copake Town Park. North Star restaurant serves American cuisine for dinner, while free WiFi and parking add convenience. Guests consistently praise the attentive staff who enhance every stay.
The price is $165
$185 total
includes taxes & fees
Nov 20 - Nov 21
the Alander
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

12. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (818 reviews)
This tranquil hotel offers sound-insulated accommodations near Housatonic River and River Walk. Guests love the helpful staff, clean rooms, indoor pool, and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking while exploring Great Barrington's nearby restaurants.
The price is $144
$160 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A lodge with a large building and a dock by a lake, surrounded by forest.

13. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,014 reviews)
This peaceful Lenox hotel overlooks a picturesque lake where spectacular sunsets unfold daily. Enjoy Indian cuisine at Mint restaurant, complimentary breakfast, and free WiFi. Just 10 minutes from Tanglewood Music Center with convenient parking.
The price is $110
$122 total
includes taxes & fees
Nov 22 - Nov 23
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A large house with a balcony and a grassy yard.

14. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (635 reviews)
Experience comfort and convenience at this motel in Great Barrington, where free WiFi and parking await. Explore nearby Monument Mountain Reservation for hiking, then return to spotless rooms with daily housekeeping and notably helpful staff.
The price is $115
$128 total
includes taxes & fees
Oct 28 - Oct 29
The Little Lion
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

15. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (931 reviews)
The price is $67
$74 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

16. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (250 reviews)
Unwind in this peaceful country retreat with a seasonal outdoor pool and complimentary gourmet breakfast. Located near Haystack Mountain State Park, the inn offers free WiFi and parking while helpful staff ensure a memorable stay in Norfolk's quiet surroundings.
The price is $190
$219 total
includes taxes & fees
Oct 28 - Oct 29
Blackberry River Inn
A covered porch with white railings and rocking chairs.

17. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (453 reviews)
Wake up to a complimentary full breakfast at this cozy East Canaan B&B. Located near Land of Nod Vineyard and Winery, the inn offers free parking and daily housekeeping. Guests consistently praise the helpful staff for making stays memorable.
The price is $105
$121 total
includes taxes & fees
Oct 28 - Oct 29
Locust Tree Bed and Breakfast LLC
A large, historic building with a prominent tower and multiple domes, surrounded by autumn foliage and a lake in the background.

18. voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG
3.5 star property
Coxsackie
9.2 out of 10, Wonderful, (425 reviews)
Experience tranquility at this peaceful hotel overlooking the river. Unwind with deep-tissue massages at the full-service spa, explore nearby parks, or relax at one of 3 bars. Just minutes from Coxsackie's train station with free WiFi and parking.
The price is $161
$180 total
includes taxes & fees
Oct 29 - Oct 30
voco James Newbury Hudson Valley by IHG
A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

19. Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (143 reviews)
Unwind at this charming Great Barrington retreat featuring complimentary breakfast, WiFi, and parking. The hotel offers a restaurant, welcoming bar, and tranquil outdoor spaces near Questing and New Marlborough Town Library.
Gedney Farm
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

20. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
This cozy motel offers complimentary WiFi and parking, making outdoor adventures hassle-free. Explore the nearby Housatonic River and River Walk, or try kayaking and mountain biking. Garden views provide a serene backdrop for your Berkshires escape.
The price is $136
$152 total
includes taxes & fees
Nov 15 - Nov 16
East Rock Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Best value hotels in Sheffield

Get more from your budget at these hotels, based on amenities, reviews, and location
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
  • Pool
9.2 out of 10, Wonderful, (1007)
Travelers like the pool and kitchen, making this a great deal.
The price is $117
$150 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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Go beyond your typical stay in Sheffield

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When is the best time to visit Sheffield?

Our prices for hotels in Sheffield are cheapest in April

Price trends for hotels in Sheffield

Pricing is based on two traveler single night rates
View properties in October
Currently viewing crowd sizes and weather for October.

October

High 15°C / low 6°C. Sunny most days.
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October, no crowd data, average high temperature 15 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
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February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -8 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 12 degrees Celsius, average low temperature 2 degrees Celsius. Cloudy most days.
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May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Sheffield

Ashley House

If you're planning a bit of sightseeing during your trip, head to Ashley House— just one of the landmarks located 3.5 mi (5.6 km) from central Sheffield.
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Learn more about Sheffield

Sheffield is well-known for its attractions such as Housatonic River and Suter Farm.

See all hotels in Sheffield
A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Check out reviews of Sheffield hotels guests love

Interior detail
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
Sheffield

10/10 Exceptional

Just a beautiful home with clean, comfortable rooms and an amazing Innkeeper. Breakfasts are elegant and delicious. We stayed here in 2025 and returned in 2026 for Labor Day weekend. Will hopefully repeat in 2027.
United States
joseph
Reviewed September 8, 2026
Wilder House Berkshires

Frequently Asked Questions

What accommodations do travelers recommend in Sheffield?

Guests like Wilder House Berkshires, Quality Inn Great Barrington and Prospect Berkshires.

Can I book a refundable accommodation in Sheffield?

If you want the flexibility to change your travel plans to Sheffield, most accommodations offer refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Sheffield if I want a vacation rental instead of a traditional hotel?

If you want to find a good alternative to a hotel, browse our selection of 23 vacation homes.

What will the weather in Sheffield be like during my vacation?

The warmest months in Sheffield are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 28°F. The rainiest months are July and August.

Why should I book my Sheffield accommodation with Hotels.com?

There are plenty of reasons to book your Sheffield travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.