Book Holiday Homes in Sheffield

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Featured Holiday Homes in Sheffield

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

East Otis
Book a stay at this family-friendly vacation home in Otis. Enjoy free WiFi, a garden, and a pool table. Popular attractions Otis Reservoir and Larkum Pond are ...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Mountain View Getaway

Mountain View Getaway

West Cornwall
Book a stay at this ski vacation home in Cornwall. Enjoy free WiFi, a garden, and ski-in/ski-out access. Popular attractions Music Mountain and West Cornwall ...
Mountain View Getaway
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy in-room jetted tubs, an in-room coffeemaker, and in-room fireplaces. Popular attractions Lake Mansfield ...
Spectacular views and close to Great Barrington.
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Peace and quiet on the lake

Peace and quiet on the lake

Becket
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and patios. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry are located ...
Peace and quiet on the lake
Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Art et Industrie and Lake Mansfield Park ...
Lakeside Retreat Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
Stay at this vacation home in Copake Lake. Enjoy air conditioning. Popular attractions Copake Lake and Mosquito Island are located nearby.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!

Lenox
Stay at this vacation home in Lenox. Enjoy free WiFi, a garden, and in-room washers/dryers. Popular attractions Tanglewood Music Center and The Bookstore are ...
Heart of Lenox Walk to Town Cozy Cottage!
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Ghent
Book a stay at this family-friendly vacation home in Ghent. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Hudson Chatham Winery and ...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
The Race Mountain House

The Race Mountain House

2 out of 5
Sheffield
Stay at this vacation home in Sheffield. Enjoy patios, in-room fireplaces, and air conditioning. Popular attractions Mount Everett State Reservation and Drury ...
The Race Mountain House
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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.

Sheffield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Sheffield vacation homes are the perfect way for you to wing it.

Holiday houses in Sheffield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Sheffield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Sheffield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Sheffield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Sheffield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Sheffield Holiday Homes essential information

Accommodation
474 Holiday Homes
Lowest Price
NZ$192
Highest Price
NZ$287
Popular accommodation
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, Mountain View Getaway, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Lakeside Retreat Just You, The Lake & The View!, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Heart of Lenox Walk to Town Cozy Cottage!, Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna, The Race Mountain House

Top trending hotels in Sheffield

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street, Sheffield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$287 per night from 6 May to 7 May
NZ$287
includes taxes & fees
6 May - 7 May
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
Wilder House Berkshires
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$242 per night from 29 Apr to 30 Apr
NZ$242
includes taxes & fees
29 Apr - 30 Apr
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 14 May to 15 May
NZ$224
includes taxes & fees
14 May - 15 May
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$192 per night from 29 Apr to 30 Apr
NZ$192
includes taxes & fees
29 Apr - 30 Apr
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
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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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^Subject to availability and chosen travel dates.