Sheffield Holiday Rentals, Massachusetts: Private House Rentals

A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

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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

4.242.905 ₫

4.739.324 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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 bathroom, a bed, a desk, and a nightstand.

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

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

2. Quality Inn Great Barrington

Downtown Great Barrington

Joan

1.942.234 ₫

2.169.476 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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

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

Great Barrington

Kelly

3.719.529 ₫

4.154.715 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

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

2.151.028 ₫

2.402.697 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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

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

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

5. East Rock Inn

Great Barrington

ERIK

3.258.323 ₫

3.639.546 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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

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.

6. Monument Mountain Motel

Great Barrington

Andrea

1.549.696 ₫

1.730.947 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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.

7. Prospect Berkshires

Egremont

Conor

7.340.665 ₫

9.067.197 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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.

8. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

2.045.547 ₫

2.284.876 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A large house with a balcony and a grassy yard.

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.

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

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

9. The Little Lion

Great Barrington

Lidia

2.679.925 ₫

2.993.476 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

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

10. Little Cat Lodge

Copake Falls

Stacy

3.938.325 ₫

4.410.924 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

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.

11. The Old Inn On The Green

Great Barrington

Catherine

7.508.970 ₫

9.060.996 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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 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.

12. Blackberry River Inn

Norfolk

Donna

4.919.670 ₫

5.657.620 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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.

13. The White Hart

Salisbury

William

7.993.169 ₫

9.192.274 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

A covered porch with white railings and rocking chairs.

14. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

2.718.765 ₫

3.126.580 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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

A covered porch with wicker furniture and hanging flower baskets.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

15. The Red Lion Inn

Stockbridge

Stephan

4.078.665 ₫

5.842.234 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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 modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

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

16. the Alander

Copake

Joseph

4.272.345 ₫

4.785.026 ₫ total

includes taxes & fees

13 Nov - 14 Nov

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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

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

South Lee

Jared

3.029.481 ₫

3.890.164 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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.

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

18. Quality Inn Lee - Lenox South

Lee

Christine

2.398.986 ₫

2.679.668 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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

A tented area with lush greenery and a dining setup.

A modern hotel room with a bed, sofa, leather chair, and a small table.

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

19. Interlaken Inn & Resort

Lakeville

Stacie

6.967.806 ₫

8.012.977 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A bedroom with a wooden bed, bedside tables, a desk, and a chair.

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

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

20. Granville House

Housatonic

Cynthia

6.576.822 ₫

7.346.362 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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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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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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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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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

"Sitting around the fire pit after a long day of leaf peeping was glorious..."

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

10/10 Excellent

"New hotel with clean"

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf."

The Yankee Inn

10/10 Excellent

"Clean room. Special thank you to the cleaning and breakfast staff. Great balcony view. We will come back again."

Quality Inn Great Barrington

10/10 Excellent

"good location, friendly helpful staff"

Quality Inn Lee - Lenox South

8/10 Good

"Had a comfortable stay."

Berkshire Mountain Lodge

10/10 Excellent

"Beautiful location. Easy access to local restaurants and hiking trails."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Nice place to stay"

Berkshires Untold

8/10 Good

"Enjoyed the view and the aesthetic"

More cheap stays in Sheffield

Quality Inn Great Barrington

372 Main Street Great Barrington MA

1.942.234 ₫

2.169.476 ₫ total

8 Nov - 9 Nov

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.045.547 ₫

2.284.876 ₫ total

19 Oct - 20 Oct

includes taxes & fees

7.6/10 Good! (925 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

2.398.986 ₫

2.679.668 ₫ total

4 Nov - 5 Nov

includes taxes & fees

8.6/10 Excellent! (1,006 reviews)

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

1055 South Street Pittsfield MA

2.563.407 ₫

2.863.326 ₫ total

12 Nov - 13 Nov

includes taxes & fees

9.4/10 Exceptional! (238 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.747.096 ₫

3.068.506 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,011 reviews)

The Whitlock

16 Church St Lenox MA

3.654.156 ₫

4.081.692 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Hotels in Sheffield with star rating

Frequently asked questions

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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Book Hotels in Sheffield on Expedia.com

Find hotels in Sheffield, MA from 1.730.947 ₫

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. East Rock Inn

6. Monument Mountain Motel

7. Prospect Berkshires

8. Travelodge by Wyndham Great Barrington Berkshires

9. The Little Lion

10. Little Cat Lodge

11. The Old Inn On The Green

12. Blackberry River Inn

13. The White Hart

14. Locust Tree Bed and Breakfast LLC

15. The Red Lion Inn

16. the Alander

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

18. Quality Inn Lee - Lenox South

19. Interlaken Inn & Resort

20. Granville House

Stay near popular Sheffield attractions

Ashley House

Thom Reed UFO Monument Park

Bartholomew's Cobble

Bartholomews Cobble

Drury Preserve

Lime Kiln Farm Wildlife Sanctuary

Learn more about Sheffield

Top Sheffield Hotel Reviews

Courtyard by Marriott Lenox Berkshires

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

The Cornell Inn, Lenox & The Berkshires

The Yankee Inn

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak 'n Spruce Resort

Berkshires Untold

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

Hotels in Sheffield with star rating

Frequently asked questions

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