Sheffield Holiday Rentals, Massachusetts: Private House Rentals

A covered wooden structure with a sloped roof, surrounded by greenery and trees.

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Our top choices for Sheffield hotels

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

1. Wilder House Berkshires

Sheffield

Mark

฿6,341

฿7,083 total

includes taxes & fees

13 Sept - 14 Sept

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

Great Barrington

Bruce

฿6,123

฿6,839 total

includes taxes & fees

17 Sept - 18 Sept

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A Quality Inn sign, a brick building, and a parking lot with cars.

3. Quality Inn Great Barrington

Great Barrington

Sisile

฿3,406

฿3,804 total

includes taxes & fees

10 Sept - 11 Sept

A modern hotel lobby with seating areas, tables, and a reception desk.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A kitchenette with a microwave, coffee maker, and coffee cups.

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Great Barrington

BJORN

฿4,342

฿4,850 total

includes taxes & fees

15 Sept - 16 Sept

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A house with a stone patio and wooden stools.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

5. Little Cat Lodge

Copake Falls

Kees

฿5,891

฿6,598 total

includes taxes & fees

9 Sept - 10 Sept

A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

An outdoor patio with wooden tables and chairs, surrounded by greenery.

A spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.

A wooden sign with "GEDNEY FARM" written on it, surrounded by lush greenery and purple flowers.

6. Gedney Farm

Great Barrington

Jane

฿7,549

฿8,281 total

includes taxes & fees

9 Sept - 10 Sept

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

A two-story building with a flat roof, solar panels, and a small patio area.

7. Locust Tree Bed and Breakfast LLC

East Canaan

Nicholas

฿3,454

฿3,972 total

includes taxes & fees

9 Sept - 10 Sept

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

A grand hallway with a chandelier, a staircase, and a table with flowers.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

8. Blackberry River Inn

Norfolk

Rachel

฿4,934

฿5,674 total

includes taxes & fees

10 Sept - 11 Sept

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

9. Monument Mountain Motel

Great Barrington

Analisia

฿2,812

฿3,141 total

includes taxes & fees

9 Sept - 10 Sept

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

10. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Kevin

฿2,796

฿3,123 total

includes taxes & fees

9 Sept - 10 Sept

A dining table with pastries, a coffee pot, and a vase of sunflowers.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

11. Granville House

Housatonic

Nicole

฿7,368

฿8,230 total

includes taxes & fees

13 Sept - 14 Sept

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

12. East Rock Inn

Great Barrington

ERIK

฿4,770

฿5,328 total

includes taxes & fees

22 Sept - 23 Sept

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

13. Quality Inn Lee - Lenox South

Lee

Christine

฿3,327

฿3,716 total

includes taxes & fees

29 Sept - 30 Sept

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

14. The Little Lion

Great Barrington

Anne

฿3,700

฿4,133 total

includes taxes & fees

9 Sept - 10 Sept

A bedroom with a large bed, a chair, and a window with curtains.

A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A covered porch with a dining area, a sofa, and decorative wall art.

15. The White Hart

Salisbury

William

฿11,328

฿13,027 total

includes taxes & fees

15 Sept - 16 Sept

A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

A kitchenette with a refrigerator, coffee maker, toaster, and bread display.

A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

A motel with multiple rooms, a well-maintained lawn, and a stone pathway.

16. Econo Lodge Lee - Great Barrington

Lee

Anna

฿2,153

฿2,405 total

includes taxes & fees

29 Sept - 30 Sept

A wooden deck with a swing chair and a bench overlooking a lake.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

A modern bar area with a counter, bar stools, and a variety of bottles.

A tented area with lush greenery and a dining setup.

17. Interlaken Inn & Resort

Lakeville

Stacie

฿6,289

฿7,232 total

includes taxes & fees

22 Sept - 23 Sept

A red building with a sign reading "Shaker Mill Inn."

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

18. Shaker Mill Inn

West Stockbridge

Mervin

฿4,901

฿5,376 total

includes taxes & fees

9 Sept - 10 Sept

A building with a porch and multiple windows, surrounded by purple flowers.

A café with a display case, a frozen food section, and a marketplace sign.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A living room with a sofa, armchair, coffee table, and a patterned rug.

19. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Linda

฿3,375

฿4,413 total

includes taxes & fees

14 Sept - 15 Sept

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.

A snow-covered landscape with a house and a sign that reads "the brooks".

20. The Brooks Motel

Hillsdale

Nelson

฿4,343

฿4,864 total

includes taxes & fees

9 Sept - 10 Sept

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Stay near popular Sheffield attractions

Ashley House

Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history.

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Thom Reed UFO Monument Park

8.0/10 (1 review)

America's first officially documented UFO encounter is commemorated at this riverside park in Sheffield. Explore plaques about the Reed family's 1969 experience while enjoying Housatonic River views.

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Bartholomews Cobble

Twin rocky knolls form this National Natural Landmark, home to one of North America's most diverse fern collections. Explore five miles of trails through forests and riverbanks for exceptional wildlife viewing.

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Bartholomew's Cobble

10.0/10 (1 review)

This National Natural Landmark features twin rocky knolls and North America's most diverse fern collection. Explore its trails through varied ecosystems while watching for peregrine falcons and rare plants.

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Drury Preserve

Explore diverse ecosystems along a serene 2.4-mile trail through hemlock forests and calcareous wetlands. Cross wooden boardwalks to a tranquil pond where great blue herons and other wildlife await.

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Lime Kiln Farm Wildlife Sanctuary

This wildlife sanctuary showcases diverse plant species across limestone ridges and conifer forests. Explore trails to spot numerous butterfly species and Pileated Woodpeckers in the tranquil Berkshires landscape.

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Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

See all hotels in Sheffield

Top Sheffield Hotel Reviews

Wilder House Berkshires

10/10 Excellent

"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."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Very clean room the staff were very pleasant. The breakfast was pretty decent. The only issue we had was parking that didn’t seem to be enough spots for the hotel when we came back from a concert at Tanglewood. Every spot at the hotel was taken. Luckily somebody left otherwise the place was great."

Little Cat Lodge

10/10 Excellent

"This hotel is the perfect getaway. A beautiful location and in the summer simply magical. I was impressed with the grounds, they are beautifully maintained and the poll a big plus! The beds are some of the most comfortable in the this region!"

Howard Johnson by Wyndham Lenox

10/10 Excellent

"We were in town for a concert and skeptical at first but when we arrived at our room it was very clean, the front desk was quick and pleasant, would definitely recommend as a nice place to stay!"

Quality Inn Lee - Lenox South

8/10 Good

"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."

Hideaway Inn Lenox

10/10 Excellent

"We reserved this Inn because of its close proximity to Tanglewood. Easy check-in and check-out. The queen bed was super comfortable. Room clean. It was nice to have coffee available 24/7. Would stay here again!"

The Whitlock

10/10 Excellent

"Great quiet and peaceful walkable to all local places."

Berkshire Mountain Lodge

10/10 Excellent

"Staff is very friendly and helpful."

Berkshires Untold

10/10 Excellent

"We only stayed one evening, but the attention to detail was beautiful and the staff was friendly. Would definitely stay again."

More cheap stays in Sheffield

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

฿3,327

฿3,716 total

29 Sept - 30 Sept

includes taxes & fees

8.4/10 Very good! (1,020 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿3,406

฿3,804 total

10 Sept - 11 Sept

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,815

฿4,262 total

22 Sept - 23 Sept

includes taxes & fees

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

฿4,166

฿4,653 total

10 Sept - 11 Sept

includes taxes & fees

9.2/10 Wonderful! (199 reviews)

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

฿4,342

฿4,850 total

15 Sept - 16 Sept

includes taxes & fees

8.8/10 Excellent! (818 reviews)

The Whitlock

16 Church St Lenox MA

฿4,725

฿5,278 total

9 Sept - 10 Sept

includes taxes & fees

8.4/10 Very good! (372 reviews)

Frequently asked questions

Where is the best place to stay in Sheffield?

Wilder House Berkshires is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are Berkshire Mountain Lodge and The Yankee Inn. See all available top hotels, or vacation rentals in Sheffield.

If I need to cancel my hotel reservation in Sheffield, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.

What are some accommodation options with pools in Sheffield?

Berkshire Mountain Lodge: Provides free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn and The Red Lion Inn are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.

What's it like staying in Sheffield?

Visitors can enjoy all that Sheffield has to offer, including the casinos and local tours. In Sheffield, there are 32 hotels and other accommodation options to choose from. Find out more about Sheffield.

What are the top places to visit in Sheffield?

Favourite places to visit include Housatonic River, Three Mile Pond Wildlife Management Area and Ashley House. A couple of additional sights to add to your itinerary are Mount Everett State Reservation and Thom Reed UFO Monument Park. Take a look at what more there is to see and do in Expedia's Sheffield guide.

What's the seasonal weather like in Sheffield?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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More ways to book

Book Hotels in Sheffield on Expedia.com

Find hotels in Sheffield, MA from ฿2,405

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Sheffield

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sheffield hotels

1. Wilder House Berkshires

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

3. Quality Inn Great Barrington

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

5. Little Cat Lodge

6. Gedney Farm

7. Locust Tree Bed and Breakfast LLC

8. Blackberry River Inn

9. Monument Mountain Motel

10. Travelodge by Wyndham Great Barrington Berkshires

11. Granville House

12. East Rock Inn

13. Quality Inn Lee - Lenox South

14. The Little Lion

15. The White Hart

16. Econo Lodge Lee - Great Barrington

17. Interlaken Inn & Resort

18. Shaker Mill Inn

19. Holiday Inn Club Vacations Oak 'n Spruce Resort

20. The Brooks Motel

Stay near popular Sheffield attractions

Ashley House

Thom Reed UFO Monument Park

Bartholomews Cobble

Bartholomew's Cobble

Drury Preserve

Lime Kiln Farm Wildlife Sanctuary

Learn more about Sheffield

Top Sheffield Hotel Reviews

Wilder House Berkshires

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Little Cat Lodge

Howard Johnson by Wyndham Lenox

Quality Inn Lee - Lenox South

Hideaway Inn Lenox

The Whitlock

Berkshire Mountain Lodge

Berkshires Untold

More cheap stays in Sheffield

Quality Inn Lee - Lenox South

Quality Inn Great Barrington

The Yankee Inn

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Whitlock

Frequently asked questions

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