Sheffield Holiday Homes from €243: Search Top House Rentals

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Sheffield holiday homes

Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

2 Jun - 3 Jun

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

Sherwood Forest

Sharon K.

includes taxes & fees

2 Jun - 3 Jun

stylish Berkshires Retreat

Lee

includes taxes & fees

2 Jun - 3 Jun

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

includes taxes & fees

7 Jun - 8 Jun

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

Sherwood Forest

Frank M.

includes taxes & fees

2 Jun - 3 Jun

Cozy Riverside Berkshires Retreat

Great Barrington

Jennifer L.

includes taxes & fees

8 Jun - 9 Jun

Treetop Hideaway in Tyringham

Monterey

Sarah B.

includes taxes & fees

2 Jun - 3 Jun

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

Chatham

Jim S.

includes taxes & fees

4 Jun - 5 Jun

View all properties

Find holiday rentals that suit your style

Private holiday homes

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Sheffield Hotel Reviews

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent

"I spilled an ENTIRE cup of cocoa I was making for my niece. The clerk on was a very kind, friendly young man named Paul. I have worked as a chef for 30 years, the cocoa went EVERYWHERE. He got a mop bucket , I started cleaning my mess up I just know what its like to walk into a mess!! Left by someone else. Paul said "you dont have to finish, ill do it no problem. He was a VERY kind young man. And he was helpful & he cleaned up the rest of the spill. I think your LUCKY to have such kind helpful employees. Just a side note. The hot tub was wayyy hotter then the thermometer( I think). It was unbearable to sit in it for more then a few minutes. And I LOVE being WARM, but everyone around( 3 others came in to use it but could not sit in it for more then a few seconds. Maybe lower it a bit now that winter is GONE!! Also housekeeping was knocking at our door before it was even 11 am!! Were literally just finishing packing up, and shes knocking. I travel extensively. I know check out is 11am. Unless your in vegas snd pay 30$ for a late check out. Beautiful , clean awesome staff(Paul). Clean!! Well be back!"

Wilder House Berkshires

10/10 Excellent

"We can't say enough lovely things about Wilder House and especially Brad! We truly enjoyed our time at Wilder House--it's quiet yet convenient to so many attractions in the Berkshires, and the property itself is beautiful and our room was comfortable--but what made it special was the host. We had a great time getting to know him and felt well-cared for during our stay. Brad even checked in on us when we were running behind for check in, to make sure that everything was okay. And as so many others have mentioned, the breakfast was delicious. (We had an omelet made with eggs from a neighbor of Wilder House--delightful!) We hope to stay here again next time we're in the Berkshires!"

Berkshires Untold

4/10 Poor

"From the time we showed up and told that they had no reservation for us, when we paid in full for a king suite, until we left, this experience was frustrating and full of problems. All king suites were sold out, including the one we paid for! We were told we would receive a 50% credit back to our credit card and we have yet to see that. The coffee was either unavailable/self serve or pretty bad. We experienced all of these. The check in person was somewhat helpful but was limited as to what we/they could do to remedy the whole situation. Communications from the upper management have gone unanswered The room we were given instead was very small, no amenities as stated in our reservation, etc I could go on with the sub par remedies, lack of communication and any follow through. Ingress and egress from this hotel is extremely difficult and dangerous, coming from the main four lane highway with no lights. The whole experience was Not pleasant at all on a trip that was a milestone for us. We will not be returning"

Monument Mountain Motel

10/10 Excellent

"Immaculately clean, comfortable bed; the two most important things. We've stayed at more charming places in Great Barrington, but our usual B&B required two nights and we only wanted one. Nothing fancy, no frills, but ultimately quite satisfactory. We would stay here again. P.S. we found some charm and a nice breakfast at the Holli Cafe."

Find out more about Sheffield

Sheffield Holiday Homes information

Number of reviews	192
Accommodation	434 Holiday Homes
Lowest Price	€243
Highest Price	€1,256

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sheffield holiday homes

Cheerful 3-bedroom cottage with woodstove