Search Vacation Homes in Sheffield

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Vacation Homes in Sheffield

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (13)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is AED 2,134
AED 3,660 total
includes taxes & fees
12 Aug - 13 Aug
Spacious 5-bedroom house in charming Lee with WiFi
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
A Design-Lover's Retreat in Litchfield County, CT - Escape to Pennybrook Cottage
Fridge, microwave, oven, stovetop

A Design-Lover's Retreat in Litchfield County, CT - Escape to Pennybrook Cottage

10.0 out of 10, Exceptional, (2)
"Our family so enjoyed staying at your beautifully decorated, comfortable, fully stocked home. Everything you provided made for a lovely stay in the quaint Falls Village location. "
A Design-Lover's Retreat in Litchfield County, CT - Escape to Pennybrook Cottage
Mountain View Getaway
Outdoor dining

Mountain View Getaway

10.0 out of 10, Exceptional, (54)
"Such a magical place…always enjoy our stay. The home is so comfy - the hosts are amazing. "
Mountain View Getaway
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Property grounds

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great stay. The host was great with communicating directions and details for the home and even shared local recommendations. We appreciated their quick response to our questions, too. "
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Falls Reach In The Heart of Copake
Property grounds

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake
Charming cottage with lake access, wood burning fire place, and WiFi
Smart TV, fireplace

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (5)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Woodland A-Frame
Exterior

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Stylish Pine Plains Home Near Parks & Hiking!
Fridge, microwave, stovetop, dishwasher

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (14)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (8)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
CT Gate House Goshen CT, Gate House Goshen CT
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is AED 975
AED 3,072 total
includes taxes & fees
27 Jul - 28 Jul
CT Gate House Goshen CT, Gate House Goshen CT
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"
Spectacular views and close to Great Barrington.
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is AED 1,017
AED 1,522 total
includes taxes & fees
6 Aug - 7 Aug
Home in Great Barrington
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Terrace/patio

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

10.0 out of 10, Exceptional, (3)
"Home was very nice and as described. Perfect for our needs "
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Secluded Family Home in Serene Stockbridge Woods
Dining

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Charming Home with Fireplace and Indoor Pool in Sharon, CT
Terrace/patio

Charming Home with Fireplace and Indoor Pool in Sharon, CT

10.0 out of 10, Exceptional, (1)
"Our family had a wonderful stay at the beautiful, clean, peaceful Hoyt House. There was plenty of space to gather together as well as spread out. The daffodils were beginning to bloom and there is the sight and sound of a running stream behind the home. We were close to fun things to explore like the Audubon, covered bridge, and Kent waterfalls. Great bakery, restaurants, grocery a short drive away. The heated indoor swimming pool was the biggest hit. We hope to have the opportunity to...
Charming Home with Fireplace and Indoor Pool in Sharon, CT
Charming 3-bedroom farmhouse in Lenox
Terrace/patio

Charming 3-bedroom farmhouse in Lenox

Charming 3-bedroom farmhouse in Lenox
Charming 2-bedroom house in Copake with AC, WiFi. Enjoy your stay
Beach

Charming 2-bedroom house in Copake with AC, WiFi. Enjoy your stay

Charming 2-bedroom house in Copake with AC, WiFi. Enjoy your stay
Country Living just minutes from Everything!
Fridge, microwave, oven, stovetop

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free