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

Sheffield Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Sheffield holiday rentals

Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is HK$3,135
HK$5,410 total
includes taxes & fees
23 Jun - 24 Jun
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,857
HK$3,948 total
includes taxes & fees
12 Jul - 13 Jul
Cheerful 3-bedroom cottage with woodstove
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is HK$1,567
HK$2,634 total
includes taxes & fees
21 Jun - 22 Jun
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is HK$1,842
HK$2,325 total
includes taxes & fees
22 Jun - 23 Jun
BLUSH: Boutique TINY home*private spa*walk to town
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,792
HK$3,769 total
includes taxes & fees
1 Jul - 2 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is HK$1,803
HK$2,976 total
includes taxes & fees
21 Jun - 22 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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$2,500
HK$4,912 total
includes taxes & fees
22 Jun - 23 Jun
Treetop Hideaway in Tyringham
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$776
HK$2,705 total
includes taxes & fees
16 Jul - 17 Jul
Real Estate: Therapy - Lake, Laundry, Love it
Terrace/patio

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is HK$1,234
HK$1,945 total
includes taxes & fees
2 Jul - 3 Jul
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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$1,178
HK$2,988 total
includes taxes & fees
23 Jun - 24 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor dining

Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
8.8 out of 10, Excellent, (3 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is HK$1,693
HK$3,134 total
includes taxes & fees
23 Jun - 24 Jun
Hudson NY’S Country Serenity Guest Suite.
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is HK$1,693
HK$3,747 total
includes taxes & fees
1 Jul - 2 Jul
stylish Berkshires Retreat
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveller
The price is HK$1,869
HK$2,876 total
includes taxes & fees
22 Jun - 23 Jun
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (16 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,587
HK$2,464 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Riverside Berkshires Retreat
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,176
HK$1,492 total
includes taxes & fees
21 Jun - 22 Jun
The Brooks Motel: Exceptional Suite
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is HK$1,221
HK$4,747 total
includes taxes & fees
22 Jun - 23 Jun
NEW: Chic Modern Barn Style Home in Fun Area
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$2,250
HK$2,836 total
includes taxes & fees
21 Jun - 22 Jun
rural, serene + sophisticated space
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$3,723
HK$6,749 total
includes taxes & fees
1 Jul - 2 Jul
Spacious 5-bedroom house in charming Lee with WiFi
Shower, hair dryer, towels, soap

Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is HK$2,458
HK$4,943 total
includes taxes & fees
22 Jun - 23 Jun
Spacious Central Berkshires Home for Groups
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$2,369
HK$4,195 total
includes taxes & fees
22 Jun - 23 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Our experience at the Red Lion Inn went beyond our expectations. The entire staff was most helpful, went above and beyond to make our stay enjoyable, and treated us as if we were the only guests staying there! The inn is magnificent and we felt we were staying in a museum! The accommodation was lovely and the dining room served gourmet food. We would love to go back. If you haven’t stayed there you are missing out on a great opportunity."
Marinus 2-night trip
Posted 7 hours ago
The Red Lion Inn

Find out more about Sheffield

Search for holiday rentals in Sheffield on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheffield using one of the methods below:

  • View our selection of featured holiday rentals in Sheffield
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  • Enter your travel dates to view the best deals on holiday rentals in Sheffield while they last

Look no further and take a look at our great range of rental properties in Sheffield!

Frequently asked questions

Can I find a holiday rental in Sheffield?

Yes, there are holiday rentals close to the most popular sights in Sheffield, or you can select a more secluded option if you're looking for a relaxing stay. Sheffield is known for its casinos and local tours.

What are some of the best holiday rentals that Sheffield has to offer?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Sheffield is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and an electric kettle, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Sheffield?

With 23 Expedia holiday rentals, you're guaranteed to find just the right place for your Sheffield stay.

What’s there to see and do in Sheffield?

Housatonic River and Bartholomews Cobble are a couple of scenic spots to enjoy the outdoors, whereas Ashley House is one of the cultural attractions. While here, Mount Everett State Reservation and Thom Reed UFO Monument Park are other places worth a visit.

What are holiday rentals like in Sheffield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sheffield. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family getaway.