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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Sheffield cottages

House (3 Bedrooms) | Interior

Water-view Home in the Berkshires

Water-view Home in the Berkshires
3.0 star property
Sheffield
Water-view Home in the Berkshires
House (4 Bedrooms) | Front of property

Great Barrington Lakeside Getaway w/ Kayak & Grill

Great Barrington Lakeside Getaway w/ Kayak & Grill
3.0 star property
Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
House (4 Bedrooms) | Interior

52-acre Berkshires Farmhouse Fire Pit, Outdoor Dining + Trails Copper Kettle Farm by Avantstay

52-acre Berkshires Farmhouse Fire Pit, Outdoor Dining + Trails Copper Kettle Farm by Avantstay
3.0 star property
Ashley Falls
52-acre Berkshires Farmhouse Fire Pit, Outdoor Dining + Trails Copper Kettle Farm by Avantstay
House (4 Bedrooms) | Interior

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
3.0 star property
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"We had an amazing experience! Such a beautiful home and amazing host! We loved it! Definitely staying here again. Highly recommend! Thank you! "
United States
Diego
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
House (4 Bedrooms) | Interior

1 Mi to Vineyard: Serene Berkshires Country Escape

1 Mi to Vineyard: Serene Berkshires Country Escape
3.0 star property
Richmond
1 Mi to Vineyard: Serene Berkshires Country Escape
House (1 Bedroom) | Front of property

Lakefront Escape w/ Dock! Hudson Valley Home

Lakefront Escape w/ Dock! Hudson Valley Home
3.0 star property
Hillsdale
Lakefront Escape w/ Dock! Hudson Valley Home
House (5 Bedrooms) | Interior

Ashley Falls Home w/ Fire Pit: Hike & Ski!

Ashley Falls Home w/ Fire Pit: Hike & Ski!
3.0 star property
Ashley Falls
9.6 out of 10, Exceptional, (4 reviews)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
United States
JAY
Ashley Falls Home w/ Fire Pit: Hike & Ski!
House (3 Bedrooms) | Interior

4 Mi to Great Barrington: Berkshires Retreat!

4 Mi to Great Barrington: Berkshires Retreat!
3.0 star property
Great Barrington
4 Mi to Great Barrington: Berkshires Retreat!
House (3 Bedrooms) | Interior

Berkshires Cabin 2 Mi to Appalachian Trail!

Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Otis
Berkshires Cabin 2 Mi to Appalachian Trail!
House (4 Bedrooms) | Interior

Dog-friendly Copake Home w/ Sauna!

Dog-friendly Copake Home w/ Sauna!
3.0 star property
Copake
Dog-friendly Copake Home w/ Sauna!
House (3 Bedrooms) | Front of property

Charming Sharon Dwelling w/ Deck & Fire Pit!

Charming Sharon Dwelling w/ Deck & Fire Pit!
3.0 star property
Sharon
Charming Sharon Dwelling w/ Deck & Fire Pit!
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

6/10 Okay
"The Property is dated "
Joan 1-night trip
Posted 20 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Sheffield

Sheffield Cottages information

Number of reviews
1
Accommodation
110 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Sheffield cost?
Cottages in Sheffield range between and per night. These stays offer a chance to touch base with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Sheffield?
There are 110 cottages in Sheffield. No matter if you're taking a trip with the kids or planning a getaway with your besties, Expedia can help you find the ideal space to get back to nature.
Why book your cottage in Sheffield with Expedia?
We think a getaway should be a walk in the park, so if you're in search of cottages in Sheffield at a nice price, Expedia has your back. Save money and check in to an economical option far from the downtown buzz, or book a 5-star cottage to pamper your loved ones.
How can I find cheap cottages in Sheffield?
With Expedia's handy filter tool, booking cheap cottages in Sheffield has never been simpler. To find accommodation that are very pocket friendly, tailor your search results by budget, amenities and star rating.
What is there to do in Sheffield near my cottage?
After you've checked in to your hotel, get out and discover the incredible things Sheffield has for you to experience. Magnolia Bluffs Casino is a great attraction to add to your itinerary.