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 bedroom with a large bed, a dresser, a chair, and a mirror.

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

฿6,649

฿7,426 total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

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.

2. Quality Inn Great Barrington

Great Barrington

Joan

฿2,538

฿2,835 total

includes taxes & fees

1 Nov - 2 Nov

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.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

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

Great Barrington

Kelly

฿4,817

฿5,380 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A breakfast area with a counter, coffee machine, and a display of pastries.

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

Maria Dulce

฿2,783

฿3,109 total

includes taxes & fees

10 Nov - 11 Nov

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

A motel with a parking lot and several cars parked.

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

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

5. Monument Mountain Motel

Great Barrington

Andrea

฿2,007

฿2,241 total

includes taxes & fees

1 Nov - 2 Nov

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

6. East Rock Inn

Great Barrington

ERIK

฿4,425

฿4,943 total

includes taxes & fees

11 Nov - 12 Nov

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

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

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

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

7. Gedney Farm

Great Barrington

Terri

฿6,763

฿7,419 total

includes taxes & fees

2 Nov - 3 Nov

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

A house with a stone patio and wooden stools.

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

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

8. Little Cat Lodge

Copake Falls

Kees

฿5,100

฿5,712 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

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

9. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

฿2,649

฿2,959 total

includes taxes & fees

12 Oct - 13 Oct

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

A white two-story house with a front door, windows, and a chimney.

A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

10. The Old Inn On The Green

Great Barrington

Catherine

฿9,724

฿11,733 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A room with a fireplace, two striped armchairs, and a floral drape.

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

11. Blackberry River Inn

Norfolk

Donna

฿6,371

฿7,326 total

includes taxes & fees

13 Oct - 14 Oct

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

12. Prospect Berkshires

Egremont

Conor

฿9,506

฿11,742 total

includes taxes & fees

10 Nov - 11 Nov

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

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

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

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.

13. The White Hart

Salisbury

William

฿30,278

฿34,819 total

includes taxes & fees

24 Oct - 25 Oct

A large house with a balcony and a grassy yard.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

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.

14. The Little Lion

Great Barrington

Lidia

฿3,470

฿3,876 total

includes taxes & fees

18 Oct - 19 Oct

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

A covered porch with white railings and rocking chairs.

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

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

15. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

฿3,521

฿4,049 total

includes taxes & fees

12 Oct - 13 Oct

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

A dog standing at a door entrance with a wooden floor and a mat with paw prints.

16. the Alander

Copake

Thomas

฿5,700

฿6,384 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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.

17. Granville House

Housatonic

Cynthia

฿8,517

฿9,513 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

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

South Lee

Jared

฿3,923

฿5,038 total

includes taxes & fees

13 Oct - 14 Oct

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

19. The Red Lion Inn

Stockbridge

Stephan

฿5,282

฿7,565 total

includes taxes & fees

3 Nov - 4 Nov

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

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

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

20. Quality Inn Lee - Lenox South

Lee

Christine

฿3,107

฿3,470 total

includes taxes & fees

1 Nov - 2 Nov

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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.

See properties

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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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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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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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

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Property was clean, staff friendly and helpful. Room was clean, tv channels were plentiful. Starbucks in lobby was extra nice and convenient. Overall great experience."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The room was incredible. Just need to be a little friendly at the arrival."

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

10/10 Excellent

"We requested a room on the first floor in advance. When we got there there were aware and assigned us accordingly! Staff very accommodating to our questions and food inquiries"

Berkshires Untold

10/10 Excellent

"Great, we'll run hotel"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Nice motel located on Laurel Lake. Convenient location. We did not upgrade to a room with a view of lake, but should consider. Lovely breakfast with big windows on the lake. Everything worked fine, would stay again."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Lovely room, comfortable bed and a nice breakfast."

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"Excellent room! Clean and good breakfast!"

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

the Alander

10/10 Excellent

"I wanted to sit by the firepit with my delicious Lobster Bisque from their restaurant and Reid jumped in right away and offered to start up the Firepit for me. I love the attention to the guest. It's the little things. Thank you for a good night's rest."

More cheap stays in Sheffield

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿2,538

฿2,835 total

1 Nov - 2 Nov

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

฿2,649

฿2,959 total

18 Oct - 19 Oct

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

฿3,107

฿3,470 total

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

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

1055 South Street Pittsfield MA

฿3,319

฿3,708 total

8 Nov - 9 Nov

includes taxes & fees

9.2/10 Wonderful! (234 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,554

฿3,970 total

1 Nov - 2 Nov

includes taxes & fees

The Whitlock

16 Church St Lenox MA

฿4,929

฿5,506 total

2 Nov - 3 Nov

includes taxes & fees

8.4/10 Very good! (395 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 Quality Inn Great Barrington. 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, Suter Farm and Ashley House. A couple of additional sights to add to your itinerary are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. 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 ฿2,241

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. Quality Inn Great Barrington

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

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

5. Monument Mountain Motel

6. East Rock Inn

7. Gedney Farm

8. Little Cat Lodge

9. Travelodge by Wyndham Great Barrington Berkshires

10. The Old Inn On The Green

11. Blackberry River Inn

12. Prospect Berkshires

13. The White Hart

14. The Little Lion

15. Locust Tree Bed and Breakfast LLC

16. the Alander

17. Granville House

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

19. The Red Lion Inn

20. Quality Inn Lee - Lenox South

Stay near popular Sheffield attractions

Ashley House

Thom Reed UFO Monument Park

Bartholomews Cobble

Drury Preserve

Bartholomew's Cobble

Lime Kiln Farm Wildlife Sanctuary

Learn more about Sheffield

Top Sheffield Hotel Reviews

Courtyard by Marriott Lenox Berkshires

Holiday Inn Club Vacations Oak 'n Spruce Resort

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

Berkshires Untold

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Cornell Inn, Lenox & The Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Quality Inn Lee - Lenox South

the Alander

More cheap stays in Sheffield

Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

Quality Inn Lee - Lenox South

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

The Yankee Inn

The Whitlock

Frequently asked questions

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