Sheffield Vacation Rentals

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Browse Select Sheffield Vacation Homes

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is CA $328
CA $695 total
includes taxes & fees
Sep 3 - Sep 4
Cheerful 3-bedroom cottage with woodstove

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

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is CA $224
CA $551 total
includes taxes & fees
Sep 3 - Sep 4
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (2)
"The property was great and the house was huge even for all 12 of us "
The price is CA $245
CA $1,014 total
includes taxes & fees
Aug 24 - Aug 25
CT Gate House Goshen CT, Gate House Goshen CT

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is CA $221
CA $544 total
includes taxes & fees
Sep 3 - Sep 4
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Charming Retreat at Stone Hill Estate – Nature Meets Luxury

10.0 out of 10, Exceptional, (1)
"Great experience overall! Property is beautiful and the guest home is situated nicely with access to the backyard and pond. Everything was very clean and well kept with everything in the home that we needed. The hosts were very kind and welcomed us making the stay enjoyable. Would recommend. "
The price is CA $553
CA $984 total
includes taxes & fees
Aug 26 - Aug 27
Charming Retreat at Stone Hill Estate – Nature Meets Luxury

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is CA $518
CA $715 total
includes taxes & fees
Aug 25 - Aug 26
Bungalow in the Berkshires

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is CA $260
CA $419 total
includes taxes & fees
Sep 1 - Sep 2
Home in Great Barrington

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"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."
The price is CA $315
CA $717 total
includes taxes & fees
Sep 1 - Sep 2
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is CA $257
CA $705 total
includes taxes & fees
Aug 26 - Aug 27
Perfect House In Hillsdale, Brings Friends & Fam

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
The price is CA $449
CA $788 total
includes taxes & fees
Sep 2 - Sep 3
Great Barrington Get Away

Experience Timeless Elegance in The Edith Wharton Room!

The price is CA $287
CA $416 total
includes taxes & fees
Sep 1 - Sep 2
Experience Timeless Elegance in The Edith Wharton Room!

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $588
CA $1,103 total
includes taxes & fees
Sep 2 - Sep 3
Spacious 5-bedroom house in charming Lee with WiFi

The George is an elegant restored home in the Hudson Valley

9.2 out of 10, Wonderful, (5)
"Nice big house in a quiet location. "
The price is CA $796
CA $1,292 total
includes taxes & fees
Aug 27 - Aug 28
The George is an elegant restored home in the Hudson Valley

rural, serene + sophisticated space

10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
The price is CA $413
CA $607 total
includes taxes & fees
Sep 14 - Sep 15
rural, serene + sophisticated space

Cozy Carriage House room with a double bed and private balcony

The price is CA $331
CA $472 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Carriage House room with a double bed and private balcony

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is CA $353
CA $499 total
includes taxes & fees
Sep 1 - Sep 2
Historic Susan B. Anthony Room - Cozy & Charming Stay

Elegant Carriage House room with a queen bed and private patio.

The price is CA $309
CA $444 total
includes taxes & fees
Sep 3 - Sep 4
Elegant Carriage House room with a queen bed and private patio.

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

The price is CA $453
CA $632 total
includes taxes & fees
Sep 1 - Sep 2
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is CA $497
CA $689 total
includes taxes & fees
Sep 7 - Sep 8
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Elegant suite with a king bed, fireplace, and kitchenette.

The price is CA $563
CA $773 total
includes taxes & fees
Sep 1 - Sep 2
Elegant suite with a king bed, fireplace, and kitchenette.
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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