Vacation rentals in Sheffield

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Top-rated vacation rentals in Sheffield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Cabin in Sheffield

4.81 out of 5 average rating, 246 reviews

Log Cabin - playroom, fireplace, skiing - $0 fees

Escape to a private acre of forest in the Berkshires near Great Barrington. Our large post and beam log cabin has been updated with all the modern essentials like WiFi, streaming channels, open kitchen, outdoor deck, gym/yoga studio, ping pong table and a screened porch for those beautiful warm evenings. If you have young children, you will love the separate playroom stocked with toys, books and games. For hikers, the AT is 1 hour hike from the front porch. 2:15 from NYC and 2:30 from BOS

Apr 26 – May 3

$235 per night
Guest favorite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Apr 5 – 12

$139 per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Sep 14 – 21

$92 per night

Popular amenities for Sheffield vacation rentals

Stay near Sheffield's top sights

The Pass | Marijuana Dispensary in the Berkshires3 locals recommend
Race Brook Lodge5 locals recommend
Bartholomew's Cobble Reservation45 locals recommend
The Marketplace Kitchen and Cafe20 locals recommend
Bash Bish Brew & Que4 locals recommend
The Bridge Restaurant7 locals recommend

Other great vacation rentals in Sheffield

Guest favorite

Home in Sheffield

4.93 out of 5 average rating, 111 reviews

A Private Peninsula Retreat In The Berkshires!

Mar 3 – 10

$354 per night
Guest favorite

Bungalow in Hillsdale

4.86 out of 5 average rating, 129 reviews

Copake Lake & Catamount/Berkshires Cottage

Apr 26 – May 3

$98 per night
Guest favorite

Home in Egremont

4.93 out of 5 average rating, 254 reviews

Modern Farm House 5 minutes from Great Barrington

Jun 21 – 28

$399 per night
Guest favorite

Vacation home in Great Barrington

4.94 out of 5 average rating, 131 reviews

Home in Great Barrington. Steps from downtown!

Nov 25 – Dec 2

$231 per night
Guest favorite

Farm stay in Ancram

4.95 out of 5 average rating, 257 reviews

Relaxing secluded stay with loving social animals.

Jan 15 – 22

$137 per night
Guest favorite

Apartment in Millerton

4.8 out of 5 average rating, 230 reviews

Gardens Galore and Village Whimsy Retreat

Oct 25 – Nov 1

$89 per night
Guest favorite

Cottage in Copake Falls

4.9 out of 5 average rating, 315 reviews

Beautiful cottage in Copake Falls

Jun 16 – 23

$135 per night
Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 234 reviews

Artist Cottage

Dec 14 – 21

$175 per night
Guest favorite

Barn in Hillsdale

4.97 out of 5 average rating, 116 reviews

Hudson Valley Hilltop Barn

Apr 17 – 24

$828 per night
Guest favorite

Guest suite in Sheffield

5.0 out of 5 average rating, 59 reviews

The Sunset Suite~Great South Berkshire Location!

May 8 – 15

$145 per night
Guest favorite

Cottage in Sheffield

5.0 out of 5 average rating, 17 reviews

The Blue Elm - A Historic Country Cottage

Dec 20 – 27

$225 per night
Guest favorite

Home in Sheffield

5.0 out of 5 average rating, 26 reviews

The Kellogg House in the Heart of The Berkshires

May 1 – 8

$206 per night

Quick stats about vacation rentals in Sheffield

Total rentals

90 properties

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

3.7K reviews

Nightly prices starting at

$100 before taxes and fees

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Sheffield?

    Four-legged friends are welcome in Sheffield. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Do house rentals in Sheffield have a kitchen?

    Absolutely! We offer over 50 house rentals with a kitchen in Sheffield. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Sheffield?

    Experience the best of Sheffield with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Sheffield have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Sheffield. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Sheffield?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with a kitchen, over 50 homes with wifi, over 50 homes with free parking, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Sheffield?

    Sheffield has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Sheffield?

    Yes! Work meets play with ease at over 40 vacation rentals in Sheffield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Sheffield have wifi?

    Absolutely! We offer over 50 house rentals with wifi in Sheffield. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore