Sheffield Vacation Homes

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

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Our top choices for Sheffield holiday homes

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

HK$3,226 total

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

2. Home in Great Barrington

Great Barrington

HEATHER G.

HK$2,416 total

includes taxes & fees

15 Sept - 16 Sept

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

3. Riverside Retreat in the Berkshires

Great Barrington

Kelly B.

HK$2,466 total

includes taxes & fees

21 Sept - 22 Sept

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

4. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

HK$2,496 total

includes taxes & fees

25 Sept - 26 Sept

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

5. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

HK$4,332 total

includes taxes & fees

14 Sept - 15 Sept

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

6. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

HK$2,278 total

includes taxes & fees

16 Sept - 17 Sept

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

7. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

HK$4,526 total

includes taxes & fees

21 Sept - 22 Sept

A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

8. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Hillsdale

HK$5,268 total

includes taxes & fees

13 Sept - 14 Sept

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Top Sheffield Hotel Reviews

The Yankee Inn

8/10 Good

"Beautiful views, friendly and responsive staff, property well kept. I would have given the highest praise except the indoor pool was closed for painting and maintenance. When I booked there was no notice in the website or Expedia. Since they had an outdoor pool and it was early fall, we swam theredes"

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

8/10 Good

"Stayed overnight for an event at tanglewood, and there’s so much to love about this hotel! Lobby is modern and comfortable, room was a queen suite. The beds were very comfortable and room was immaculately clean. The room could use more electrical outlets, and lighting. The only issue I had was the breakfast was served from 6-10 am on a weekend. By 10, the breakfast area was completely closed up, and all trash cans in the dining area were overflowing. There was one staff member taking out trash, and all the tables were dirty or sticky. It would have been nice to get a muffin or something with coffee to head out for the day. Overall, a great stay, would recommend!"

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Check-in was easy and the desk staff efficient. Breakfast was good as expected and breakfast area clean. Unusual to have to fill out a form the night in advance if you wanted the room cleaned or fresh towels. Great location with good dining options close by."

Little Cat Lodge

10/10 Excellent

"Beautiful and peaceful little lodge with easy access to all the wonderful things in the area (Catamount, Lakes etc..). Pool is very tranquil and each room has Mountain views. The lodge is artfully designed as well, providing a luxury feeling. I only wish 1) the indoor common area was open for guests at any time (but I assume this is a cost/staff issue) 2) there as espessso / coffee/ tea available for guests at a wider ranger of hours (only available at continental breakfast or kureg in room). But these would only be added luxuries and did not materially detract from absolutely delightful stay!!"

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