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

Coffee/tea maker, fridge, microwave, oven

1. Home in Great Barrington

Great Barrington

HEATHER G.

HK$3,206 total

includes taxes & fees

12 Aug - 13 Aug

3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Great Barrington

Mary R.

3. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

HK$2,979 total

includes taxes & fees

13 Aug - 14 Aug

4. Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington

James M.

HK$13,331 total

includes taxes & fees

2 Aug - 3 Aug

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

Great Barrington

Roberta

HK$10,417 total

includes taxes & fees

6 Aug - 7 Aug

6. 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$5,090 total

includes taxes & fees

31 Aug - 1 Sept

7. Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

Anne S.

8. Stockbridge In-town Escape

Stockbridge

HK$4,949 total

includes taxes & fees

30 Aug - 31 Aug

9. stylish Berkshires Retreat

Lee

Donna K.

HK$3,557 total

includes taxes & fees

3 Aug - 4 Aug

10. Renovated Downtown Great Barrington House

Great Barrington

"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...

Anonymous traveller

HK$19,072 total

includes taxes & fees

23 Aug - 24 Aug

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

Sherwood Forest

Frank M.

HK$3,508 total

includes taxes & fees

12 Aug - 13 Aug

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

Sherwood Forest

Sharon K.

HK$3,532 total

includes taxes & fees

12 Aug - 13 Aug

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

Chatham

Jessica V.

HK$3,171 total

includes taxes & fees

9 Aug - 10 Aug

14. Spacious Central Berkshires Home for Groups

Lee

Beth S.

HK$5,283 total

includes taxes & fees

31 Aug - 1 Sept

15. NEW: Chic Modern Barn Style Home in Fun Area

Pine Plains

Estefany G.

HK$6,196 total

includes taxes & fees

18 Aug - 19 Aug

16. rural, serene + sophisticated space

Red Hook

BRIAN PATRICK M.

HK$3,654 total

includes taxes & fees

25 Aug - 26 Aug

17. A Country Lodge Straight Out of the Pages of a Great Novel

Pine Plains

Hessie S.

HK$11,552 total

includes taxes & fees

2 Aug - 3 Aug

18. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

HK$1,752 total

includes taxes & fees

5 Aug - 6 Aug

19. Charming Hudson Valley Escape | Heated Pool & Fire Pit

Claverack-Red Mills

jessica c.

HK$7,277 total

includes taxes & fees

12 Aug - 13 Aug

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

Sherwood Forest

HK$2,541 total

includes taxes & fees

26 Aug - 27 Aug

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Top Sheffield Hotel Reviews

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

10/10 Excellent

"The hotel only 1 year old and nicely remodeled."

The Red Lion Inn

8/10 Good

"I gotta admit, I was nervous about staying at the Red Lion Inn. I knew it was popular, but I stayed in their "sister" place (the Little Lion) once because it was the only available hotel room in the area at short notice and that place is a DISASTER. However, now I understand why people who love the Red Lion Inn LOVE the Red Lion Inn. It's not pristine & shiny in a new hotel kinda way. But it's also the exact opposite of a bland, chain hotel with no character or interest. 250y of history pours out of every inch of this place, and in a good way. I didn't get a chance to take advantage of the gym, pool, or other amenities, though did eat in the courtyard one lunchtime and that was good. The staff are very attentive and appear to take real pride in working in such an iconic hotel. My only criticism is that I don't think the cleaning is quite up to scratch. Harder to clean 250yo hotel with rugs over ancient wood floors than a new construction with LVP, but findings long blonde hairs on my hotel room wasn't something I enjoyed (my entire family is either red or brunette). Would I stay there again? Yes. Room prices in the summer are insane, like most places in the Berkshires, but that's when I have to go to the Berkshires, so if they don't get my business in the future, it'll be because there are no rooms available or for some reason a different town is a better choice of location, not because I don't want to stay here. 1 word of warning: have dog? Call to make your reservation."

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