The 10 best holiday rentals in Sheffield, USA | Booking.com
Skip to main content

Holiday Rentals in Sheffield

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Sheffield

The best holiday rentals in Sheffield

Check out our pick of great holiday rentals in Sheffield

Filter by:

Review score

Wainwright Inn

Great Barrington (Near Sheffield)

Boasting a garden and views of garden, Wainwright Inn is a bed and breakfast set in a historic building in Great Barrington, 15 km from Norman Rockwell Museum.

G
Galadriel
From
United States
I will definitely be back. The place is charming, quiet and full of history. The room was spacious and comfortable and well-appointed. The breakfast was incredible, always garnished with herbs fresh from the garden.
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 43 reviews
Price from
US$171.35
1 night, 2 adults

Granville House

Great Barrington (Near Sheffield)

Situated within 10 km of Norman Rockwell Museum and 17 km of Tanglewood Musical Center, Granville House features rooms with air conditioning and a private bathroom in Great Barrington.

J
Jochen und Cosima
From
Switzerland
Perfect place to relax. We loved it.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 135 reviews
Price from
US$200
1 night, 2 adults

Kellogg Haus

Falls Village (Near Sheffield)

Offering quiet street views, Kellogg Haus is an accommodation situated in Falls Village, 45 km from Abbey of Regina Laudis and 46 km from Flanders Nature Center.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 14 reviews
Price from
US$360
1 night, 2 adults

Stockbridge Country Inn

Stockbridge (Near Sheffield)

Featuring a garden and views of mountain, Stockbridge Country Inn is a bed and breakfast situated in a historic building in Stockbridge, 1.5 km from Norman Rockwell Museum.

L
Leslie
From
France
Very friendly owner and lovely country inn.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 11 reviews
Price from
US$309.47
1 night, 2 adults

Walk to the Outfield of Lime Rock Park

Salisbury (Near Sheffield)

Located in Salisbury and only 49 km from Norman Rockwell Museum, Walk to the Outfield of Lime Rock Park provides accommodation with mountain views, free WiFi and free private parking.

J
Juliann
From
United States
The proprietors are delightful and responsive. They take good care of the little apartment built over a garage in a very inviting way. It has a personal touch with real privacy too. The proximity to LimeRock Race Track was our chief requirement as organizers of an annual cycling event there. Being able to cook until late at night to prep for the event, and wake at 4:45am in a very comfortable bed, and just roll over to the venue through a divine New England landscape was perfect. The best place we’ve ever stayed in for such an event.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 15 reviews
Price from
US$230
1 night, 2 adults

Devonfield Inn

Lee (Near Sheffield)

Situated just 6.1 km from Cranwell Spa & Golf Club, Devonfield Inn features accommodation in Lee with access to a garden, a shared lounge, as well as a shared kitchen.

R
Richard
From
United Kingdom
We received a very warm welcome on arrival, with a tour of the premises and great service at breakfast. Lots of parking and also places to chill outside under beautiful trees. The pool was lovely and warm. Nice touch of a free night cap tray in the lounge and communal kitchen for cups of tea and coffee throughout the day. Would stay there again in a heartbeat!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 13 reviews
Price from
US$369
1 night, 2 adults

A Meadow House

Lakeville (Near Sheffield)

Featuring a spa and wellness centre and views of the garden, A Meadow House is a bed and breakfast situated in a historic building in Lakeville, 500 m from Lime Rock Park.

H
Hannah
From
United States
The space was very cozy and felt like home. Lots of interesting tchotchkes, and lots of open space in the backyard. Loved hanging out with the cats! And there were snacks and coffee, which was lovely. The host even offered to drive me to and from the mechanic, which was so nice! I cannot wait to come back!!
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 104 reviews
Price from
US$135
1 night, 2 adults

Chambery Inn

Lee (Near Sheffield)

This historic Massachusetts bed and breakfast boasts free Wi-Fi access. Cable TV and an en suite bathroom are featured in every uniquely styled room. Ski Butternut is 13 miles away.

L
Lori
From
United States
Beautiful, huge room; stunning 4 poster bed w/ canopy.
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 36 reviews
Price from
US$249.99
1 night, 2 adults

The Cottage

Stockbridge (Near Sheffield)

Situated in Stockbridge, 3.3 km from Norman Rockwell Museum, The Cottage has a private beach area, parking on-site and rooms with free WiFi access.

J
Janis
From
United Kingdom
Carole was a fabulous, welcoming host - above and beyond. The property had everything we needed.
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 59 reviews
Price from
US$269
1 night, 2 adults

Downtown Great Barrington Enjoy Mountain Views

Great Barrington (Near Sheffield)

Boasting air-conditioned accommodation with a patio, Downtown Great Barrington Enjoy Mountain Views is situated in Great Barrington.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
All holiday rentals in Sheffield

Most booked holiday rentals in Sheffield and surroundings in the past month

See all