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.
Cabin in Sheffield
4.81 out of 5 average rating, 246 reviewsLog 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
May 23 – 30
Loft in Great Barrington
4.99 out of 5 average rating, 296 reviewsThe 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 29 – May 6
Apartment in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern 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 13 – 20
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Sheffield vacation rentals
Stay near Sheffield's top sights
Other great vacation rentals in Sheffield
Bungalow in Hillsdale
4.86 out of 5 average rating, 129 reviewsCopake Lake & Catamount/Berkshires Cottage
Apr 8 – 15
Farm stay in Ancram
4.95 out of 5 average rating, 257 reviewsRelaxing secluded stay with loving social animals.
Jan 13 – 20
Home in Sheffield
4.93 out of 5 average rating, 111 reviewsA Private Peninsula Retreat In The Berkshires!
Mar 4 – 11
Vacation home in Great Barrington
4.94 out of 5 average rating, 131 reviewsHome in Great Barrington. Steps from downtown!
Dec 12 – 19
Home in Egremont
4.93 out of 5 average rating, 254 reviewsModern Farm House 5 minutes from Great Barrington
Nov 14 – 21
Cottage in Copake Falls
4.9 out of 5 average rating, 315 reviewsBeautiful cottage in Copake Falls
Jun 15 – 22
Guesthouse in Lenox
4.94 out of 5 average rating, 271 reviewsThe Granary at House on Golden Hill
Apr 17 – 24
Apartment in Millerton
4.8 out of 5 average rating, 230 reviewsGardens Galore and Village Whimsy Retreat
Mar 4 – 11
Cottage in Sheffield
5.0 out of 5 average rating, 17 reviewsThe Blue Elm - A Historic Country Cottage
Dec 25 – Jan 1
Home in Sheffield
5.0 out of 5 average rating, 26 reviewsThe Kellogg House in the Heart of The Berkshires
Jan 11 – 18
Home in Sheffield
4.98 out of 5 average rating, 43 reviewsWalt's Place-Your Family Getaway
Jun 12 – 19
Guest suite in Sheffield
5.0 out of 5 average rating, 59 reviewsThe Sunset Suite~Great South Berkshire Location!
Jul 9 – 16
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 | ﺩ.ﺇ367 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.
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