Sheffield, MA Vacation Homes from AED 345

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

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Our top choices for Sheffield vacation homes

Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

AED 1,846 total

includes taxes & fees

12 Jul - 13 Jul

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

AED 748 total

includes taxes & fees

6 Jul - 7 Jul

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

AED 1,317 total

includes taxes & fees

16 Jul - 17 Jul

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

Sherwood Forest

Frank M.

AED 1,639 total

includes taxes & fees

7 Jul - 8 Jul

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

Sherwood Forest

Sharon K.

AED 1,755 total

includes taxes & fees

12 Jul - 13 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.

AED 2,489 total

includes taxes & fees

6 Jul - 7 Jul

Spacious Central Berkshires Home for Groups

Lee

Beth S.

AED 2,453 total

includes taxes & fees

12 Jul - 13 Jul

stylish Berkshires Retreat

Lee

Donna K.

AED 1,539 total

includes taxes & fees

8 Jul - 9 Jul

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Top Sheffield Hotel Reviews

The Little Lion

8/10 Good

"Unfortunately the power went out around 10 pm and never came back on by the time we left at 7 am. We tried reaching out to staff at the Red Lion, the parent company of the Little Lion. No one picked up the phone nor responded to our message. We had no power, no lights, no water, no A/C. Other than not being able to get a hold of staff our stay was very good."

Quality Inn Great Barrington

10/10 Excellent

"I booked the stay at Quality Inn without knowing what to expect. Getting to the hotel was easy. The location was perfect with mountains all around. Comfortable bed and just right amenities made the stay enjoyable. The breakfast sitting area was separate from the hotel and had a cottage feel, enjoyed having breakfast. Exploring the town of Great Barrington was easy as everything was walking distance. Quality Inn is right next to Town Hall. Had a perfect view of the Strawberry moon sitting on the bench outside of the town hall. It was fun to see through the window of the Great Barrington fm radio station and chatting with the DJ hen he stepped out. A must to stop at SoCo ice-cream shop delicious cold treats. People are very friendly. The Pizza at The Great Barrington Pizza house was delicious. Walking around we could feel the history that has transpired, small town vibe, the architecture. Do not miss going to Great Barrington Farmers market, it is a co-op market and Guido's family owned super market."

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

8/10 Good

"We had a lovely, one night stay here. I went with my adult son and his girlfriend to see Paul Simon at Tanglewood (which turned out to be an amazing show!) The front desk staff at the resort were friendly and accommodating; they let us use the amenities early before we could check in, which was GREAT! We hung around the outdoor pool, met a lot of nice people, and had a blast. Our suite was great. Parking was easy and plentiful and we had 2 bedrooms and each had it's own bathroom for full privacy. Full kitchen with fridge and freezer, a little living room and a nice outdoor deck overlooking the woods and a brook. It was clean, comfortable, and we had a wonderful stay. There is a grocery store just a few miles down the street for everything you need and Lenox is about 10-15 minutes away. We even saw a bear in the parking lot and he went out back in the woods where our porch was. I've never had a bear sighting. It was awesome! The only thing I can comment is the windows in the front bedroom were pretty dirty. It would have been nice it they were cleaned up. Honestly it didn't make or break our trip, just a business owner myself, I always like the feedback. But all in all, I would definitely recommend and definitely stay there again."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved this place. It was a bit dated aesthetically, but the charm outweighed that. Beds are comfortable. The setting on the lake is beautiful and its size of the hotel is lovely. Staff and guests were delightful. In retrospect, I wish I’d paid more for a lakefront room — it would’ve been worth it. Hotel is centrally located and it’s easy to get everywhere. Only negative was that there was no recycling."

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

10/10 Excellent

"Wonderful, clean and new hotel in great location between Lenox and Pittsfield. Room was lovely, bed comfortable, and breakfast offered everything you would expect. Staff was friendly and helpful. We were delighted to find this place and will definitely return next time we come to the Berkshires."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sheffield vacation homes

Cheerful 3-bedroom cottage with woodstove

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Real Estate: Therapy - Lake, Laundry, Love it

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