Best Resorts in Sheffield

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Jun 27 - Jun 29
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Jul 4 - Jul 6
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Jul 18 - Jul 20
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Aug 15 - Aug 17

Resorts in Sheffield

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Recommended hotels in Sheffield

Wilder House Berkshires
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (25)
"Always perfect! "
$145 nightly
The price is $163
Jun 30 - Jul 1
Total includes taxes and fees
Wilder House Berkshires
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (6)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
$720 nightly
The price is $804
Jun 23 - Jun 24
Total includes taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Book Your Perfect Fall Stay in the Berkshire Woods
Miscellaneous

Book Your Perfect Fall Stay in the Berkshire Woods

$617 nightly
The price is $652
Jun 22 - Jun 23
Total includes taxes and fees
Book Your Perfect Fall Stay in the Berkshire Woods
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Property grounds

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

9.2 out of 10, Wonderful, (41)
"Fantastic find, we had the best time"
$173 nightly
The price is $195
Jun 20 - Jun 21
Total includes taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Tranquil Retreat 6-BRs Total in the Berkshires
Interior

Tranquil Retreat 6-BRs Total in the Berkshires

$1,469 nightly
The price is $1,641
Jul 7 - Jul 8
Total includes taxes and fees
Tranquil Retreat 6-BRs Total in the Berkshires
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"Comfortable stay "
$129 nightly
The price is $145
Jun 26 - Jun 27
Total includes taxes and fees
Becket Motel
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

$326 nightly
The price is $364
Jun 23 - Jun 24
Total includes taxes and fees
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"Excellent bed and breakfast, room was clean and comfortable."
$281 nightly
The price is $312
Jun 25 - Jun 26
Total includes taxes and fees
Manor House Inn
CT Gate House Goshen CT, Gate House Goshen CT
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
$807 nightly
The price is $846
Jun 23 - Jun 24
Total includes taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (107)
"Very helpful and friendly staff"
$166 nightly
The price is $191
Jun 24 - Jun 25
Total includes taxes and fees
Blackberry River Inn
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (119)
"Beautiful and rustic, less than 15 minutes to Butternut and Great Barrington."
$259 nightly
The price is $284
Jun 29 - Jun 30
Total includes taxes and fees
Gedney Farm
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"2nd time here so I give it excellent review."
$240 nightly
The price is $263
Jun 23 - Jun 24
Total includes taxes and fees
Perfect Vacation Get Away - Historical New Marlborough
The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (84)
"Beautiful room and property. Perfect weekend getaway!"
$319 nightly
The price is $350
Jun 22 - Jun 23
Total includes taxes and fees
The Old Inn On The Green
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (384)
"A positively delightful B&B in a beautiful town. "
$105 nightly
The price is $121
Jun 22 - Jun 23
Total includes taxes and fees
Locust Tree Bed and Breakfast LLC
Hitching Post Country Motel
2 Double Beds | 2 bedrooms, free WiFi, bed sheets

Hitching Post Country Motel

2.5 star property
6.2 out of 10, (49)
"It was all I needed Hosts were very gracious. "
$130 nightly
The price is $150
Jun 20 - Jun 21
Total includes taxes and fees
Hitching Post Country Motel
Pilgrim Inn
1 bedroom, individually decorated, individually furnished, desk

Pilgrim Inn

2.5 star property
5.8 out of 10, (308)
"Great location but no staff at check-in or checkout!"
$86 nightly
The price is $97
Jul 20 - Jul 21
Total includes taxes and fees
Pilgrim Inn
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
$139 nightly
The price is $155
Jun 24 - Jun 25
Total includes taxes and fees
Deluxe Queen Room with 2 Queen Beds
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"Friendly staff, easy parking"
$108 nightly
The price is $120
Jul 7 - Jul 8
Total includes taxes and fees
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (381)
"The room was clean and perfect for our stay."
$86 nightly
The price is $96
Jul 7 - Jul 8
Total includes taxes and fees
Sunset Inn
Spacious 5-bedroom house in charming Lee with WiFi
Iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

$771 nightly
The price is $861
Jun 26 - Jun 27
Total includes taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
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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Frequently asked questions

What can I expect from a resort vacation in Sheffield?
Longing for a relaxing getaway? Indulge in all the comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to activities and shopping. Browse the resort options in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or hitting the golf course for an afternoon game.
What's a top resort in Sheffield?
Our highest-rated resort near Sheffield: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 12.2 mi (19.6 km) from Sheffield. Has a sauna, a fitness center, and a terrace.
What can I do in Sheffield?
Housatonic River, Magnolia Bluffs Casino, and Mount Everett State Reservation are a few of the interesting sights to visit. Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are a few additional attractions in the area that you might like.
What's the weather like in Sheffield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Sheffield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.