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

Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

HK$3,942 total

includes taxes & fees

12 Jul - 13 Jul

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

HK$1,590 total

includes taxes & fees

6 Jul - 7 Jul

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

HK$3,378 total

includes taxes & fees

29 Jun - 30 Jun

stylish Berkshires Retreat

Lee

HK$3,442 total

includes taxes & fees

28 Jul - 29 Jul

Cozy Riverside Berkshires Retreat

Great Barrington

Cristine C.

HK$2,793 total

includes taxes & fees

9 Jul - 10 Jul

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

HK$3,260 total

includes taxes & fees

29 Jun - 30 Jun

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jim S.

HK$2,995 total

includes taxes & fees

29 Jun - 30 Jun

Home in Great Barrington

Great Barrington

Anonymous traveller

HK$3,399 total

includes taxes & fees

19 Jul - 20 Jul

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

HK$2,715 total

includes taxes & fees

16 Jul - 17 Jul

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$5,114 total

includes taxes & fees

29 Jun - 30 Jun

NEW: Chic Modern Barn Style Home in Fun Area

Pine Plains

HK$5,371 total

includes taxes & fees

30 Jun - 1 Jul

rural, serene + sophisticated space

Red Hook

BRIAN PATRICK M.

HK$2,820 total

includes taxes & fees

30 Jun - 1 Jul

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

HK$3,679 total

includes taxes & fees

29 Jun - 30 Jun

Spacious 5-bedroom house in charming Lee with WiFi

Lee

Khalil S.

HK$6,754 total

includes taxes & fees

6 Jul - 7 Jul

Berkshire House Stay: 5BR/5BA

Lee

jennifer r.

HK$8,689 total

includes taxes & fees

13 Jul - 14 Jul

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

HK$10,448 total

includes taxes & fees

29 Jun - 30 Jun

Whispering Estate Guest House - A Romantic Countryside Getaway

Goshen

Andrea B.

HK$6,913 total

includes taxes & fees

29 Jun - 30 Jun

Spacious Central Berkshires Home for Groups

Lee

Beth S.

HK$5,659 total

includes taxes & fees

12 Jul - 13 Jul

The George is an elegant restored home in the Hudson Valley

Stanfordville

Eric L.

HK$8,658 total

includes taxes & fees

29 Jun - 30 Jun

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Mark Cristen J.

HK$8,593 total

includes taxes & fees

19 Jul - 20 Jul

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Top Sheffield Hotel Reviews

Quality Inn Great Barrington

8/10 Good

"I didn't like the somewhat steep stairs going to the 2nd floor. Otherwise an inexpensive but good place to stay."

Quality Inn Lee - Lenox South

8/10 Good

"All in all, it was a good value, but there was a male employee who was working when I checked in and whose behavior was similar to multiple people. I was ignored for over 10 minutes while he spoke on the phone. He issued me a card without asking for my ID and when I brought multiple packages in on a carrier, he gave me a second floor room where there’s no elevator. He was indifferent. he ignored us and I didn’t appreciate that."

Berkshire Mountain Lodge

10/10 Excellent

"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didn’t have a key to start it.) The bar was closed. The boutique was closed and there really wasn’t anywhere else you could go. We definitely will stay again, but we’ll just make sure it’s only on the days where we can access all the amenities."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Staff was helpful and friendly. Breakfast was amazing. The grounds are so beautiful . There were a number of lovely places inside and out for sitting and relaxing. We loved the welcome drink and a bottle of wine ( choice of red or white) to have in our room. We enjoyed it on our balcony with its lovely views of the main house and the yard. Unfortunately we couldn’t attend the cognac tasting as we were busy. I would love to come to the Cornell again-and again!"

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

10/10 Excellent

"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake machine! Also, the pool and hot tub were great. The area was kept clean and towels were well stocked. Our room was also very spacious and immaculate."

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