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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Sheffield holiday homes

Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,856
HK$3,945 total
includes taxes & fees
13 Apr - 14 Apr
Cheerful 3-bedroom cottage with woodstove
Smart TV, books

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,255
HK$3,089 total
includes taxes & fees
13 Apr - 14 Apr
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,142
HK$2,946 total
includes taxes & fees
12 Apr - 13 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"Great place!!"
United States
Ernesto B.
The price is HK$1,155
HK$5,455 total
includes taxes & fees
13 Apr - 14 Apr
CT Gate House Goshen CT, Gate House Goshen CT
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,607
HK$2,512 total
includes taxes & fees
13 Apr - 14 Apr
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (13 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,586
HK$2,480 total
includes taxes & fees
22 Apr - 23 Apr
Cozy Riverside Berkshires Retreat
Exterior

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

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (35 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is HK$2,811
HK$5,686 total
includes taxes & fees
22 Apr - 23 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,067
HK$4,362 total
includes taxes & fees
22 Apr - 23 Apr
Treetop Hideaway in Tyringham
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (6 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is HK$1,214
HK$2,300 total
includes taxes & fees
12 Apr - 13 Apr
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.0 out of 10, Wonderful, (2 reviews)
"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "
United States
Rochelle F.
The price is HK$1,370
HK$2,421 total
includes taxes & fees
12 Apr - 13 Apr
Renovated house. Built in 1890s. No neighbors in sight.
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is HK$2,107
HK$3,009 total
includes taxes & fees
13 Apr - 14 Apr
rural, serene + sophisticated space
Dining

The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.4 out of 10, Exceptional, (6 reviews)
"This our 3rd stay at the property and once again we thoroughly enjoyed the house and the grounds. We had an opportunity to enjoy horseback riding on site and would definitely recommend that to any visitors. The hosts were very kind and hospitable. "
United States
Eric L.
The price is HK$4,056
HK$6,697 total
includes taxes & fees
28 Apr - 29 Apr
The George is an elegant restored home in the Hudson Valley
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$3,418
HK$6,364 total
includes taxes & fees
18 Apr - 19 Apr
Spacious 5-bedroom house in charming Lee with WiFi
TV, fireplace, printers

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,433
HK$10,401 total
includes taxes & fees
14 Apr - 15 Apr
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$2,232
HK$4,024 total
includes taxes & fees
13 Apr - 14 Apr
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.8 out of 10, Exceptional, (6 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is HK$2,488
HK$4,940 total
includes taxes & fees
13 Apr - 14 Apr
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is HK$4,229
HK$6,911 total
includes taxes & fees
13 Apr - 14 Apr
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior

Secluded escape w/ hot tub + pizza oven+ fireplace

Secluded escape w/ hot tub + pizza oven+ fireplace
Taghkanic
The price is HK$3,172
HK$8,262 total
includes taxes & fees
4 May - 5 May
Secluded escape w/ hot tub + pizza oven+ fireplace
Fridge, microwave, oven, stovetop

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

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is HK$6,970
HK$11,534 total
includes taxes & fees
13 Apr - 14 Apr
A Country Lodge Straight Out of the Pages of a Great Novel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Beautiful place- beautiful views "
Yanis 1-night trip
Posted 5 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Sheffield

Sheffield Vacation Homes information

Number of reviews
210
Accommodation
437 Vacation Homes
Lowest Price
HK$2,300
Highest Price
HK$11,534

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