Vacation rentals in Sheffield

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Top-rated vacation rentals in Sheffield

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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.

May 17 – 24

G$31,324 GYD per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 256 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!

Oct 14 – 21

G$17,726 GYD per night

Guest favorite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 102 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Mar 6 – 13

G$47,014 GYD per night

Guest favorite

Apartment in Sheffield

5.0 out of 5 average rating, 319 reviews

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Dec 25 – Jan 1

G$34,503 GYD per night

Guest favorite

Apartment in Canaan

4.98 out of 5 average rating, 103 reviews

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Jun 17 – 24

G$27,353 GYD per night

Guest favorite

Guest suite in Canaan

4.98 out of 5 average rating, 293 reviews

Walk to Brewery in Historic Railroad Depot

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

Dec 5 – 12

G$33,395 GYD per night

Guest favorite

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

This cute, cozy cottage is located in the center of Hillsdale, NY on the grounds of the Second Empire landmark Mount Washington House, located in the hamlet’s National Historic District. The cottage is perfectly located between Hudson, NY and Great Barrington, MA and you can walk to stores, parks, Roe Jan Brewing Company, Taconic Ridge, the Harlem Valley Rail Trail and more. Very close to Catamount Mountain Resort, Copake Lake and Bash Bish Falls. Public EV charger located in west lot.

Jan 28 – Feb 4

G$26,378 GYD per night

Guest favorite

Home in Sheffield

4.9 out of 5 average rating, 107 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Rental #1 has 2 bedrooms, a FULLY EQUIPPED KITCHEN and it is SUPERCLEAN! (ALSO SEE THE 1 BEDROOM LISTING #2!) Fully renovated, large garden, private entrance, terrace and parking space. Two Queen size beds. High Speed WiFi. Berkshire Blend coffee/decaf, teas, milk, sugar and juice are a first morning welcome gift. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Jun 17 – 24

G$34,882 GYD per night

Guest favorite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 179 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Jul 15 – 22

G$33,630 GYD per night

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 212 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Jan 30 – Feb 6

G$149,265 GYD per night

Guest favorite

Apartment in Sheffield

4.92 out of 5 average rating, 122 reviews

Private Berkshire Barn Apartment

A private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.

Nov 30 – Dec 7

G$30,631 GYD per night

Guest favorite

Cottage in Copake Falls

4.91 out of 5 average rating, 317 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Oct 7 – 14

G$34,151 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Sheffield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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 28 – Apr 4

G$85,404 GYD per night

Guest favorite

Guest suite in New Marlborough

4.83 out of 5 average rating, 134 reviews

Comfortable Apartment sleeps two.

Oct 1 – 6

G$28,511 GYD per night

Guest favorite

Barn in Hillsdale

4.97 out of 5 average rating, 116 reviews

Hudson Valley Hilltop Barn

Aug 31 – Sep 7

G$233,742 GYD per night

Guest favorite

Farm stay in Ancram

4.95 out of 5 average rating, 264 reviews

Relaxing secluded stay with loving social animals.

Nov 12 – 19

G$34,888 GYD per night

Guest favorite

Vacation home in Great Barrington

4.94 out of 5 average rating, 139 reviews

Home in Great Barrington. Steps from downtown!

Mar 25 – Apr 1

G$56,268 GYD per night

Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 235 reviews

Artist Cottage

Nov 15 – 22

G$50,119 GYD per night

Guest favorite

Apartment in Sandisfield

4.92 out of 5 average rating, 227 reviews

Sunny Berkshire Studio Apartment

Dec 5 – 12

G$24,081 GYD per night

Guest favorite

Guest suite in Sheffield

5.0 out of 5 average rating, 59 reviews

The Sunset Suite~Great South Berkshire Location!

Nov 24 – Dec 1

G$36,016 GYD per night

Show all

Quick stats about vacation rentals in Sheffield

Total rentals
90 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.8K reviews
Nightly prices starting at
G$20,843 GYD 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 30 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 40 homes with air conditioning, over 50 homes with free parking, over 50 homes with a kitchen, over 50 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Sheffield vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Sheffield, available on Airbnb. Make a splash and soak up the sun in style!
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.
Do house rentals in Sheffield have free parking?
Absolutely! We offer over 50 house rentals with free parking in Sheffield. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Sheffield

Top-rated vacation rentals in Sheffield

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Sheffield vacation rentals

Stay near Sheffield's top sights

Other great vacation rentals in Sheffield

Home in Sheffield

Guest suite in New Marlborough

Barn in Hillsdale

Farm stay in Ancram

Vacation home in Great Barrington

Cottage in Great Barrington

Apartment in Sandisfield

Guest suite in Sheffield

Quick stats about vacation rentals in Sheffield

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Sheffield?

Do house rentals in Sheffield have a kitchen?

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

Do house rentals in Sheffield have air conditioning?

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

Are there Sheffield vacation rentals on Airbnb with pools?

Are there family-friendly vacation rentals in Sheffield?

Are there vacation rentals with a dedicated workspace in Sheffield?

Do house rentals in Sheffield have wifi?

Do house rentals in Sheffield have free parking?

Destinations to explore