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
With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from County Beach.
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Mountain View Getaway

Mountain View Getaway

West Cornwall
Located in Cornwall, this vacation home is on a lake, within a 15-minute drive of Music Mountain and West Cornwall Covered Bridge.
Mountain View Getaway
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
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Peace and quiet on the lake

Peace and quiet on the lake

Becket
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Peace and quiet on the lake
Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 10-minute drive of Art et Industrie and Housatonic River.
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
The price is AU$548 per night from 16 Apr to 17 Apr
AU$548
includes taxes & fees
16 Apr - 17 Apr
With a stay at this vacation home in Copake Lake, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.
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
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and The Bookstore.
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
Located in Ghent, this vacation home is in the mountains, a 4-minute drive from Hudson Chatham Winery and 10 minutes from High Falls Trail.
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
Located in Sheffield, this vacation home is in the mountains, within a 10-minute drive of Mount Riga State Park and Drury Preserve.
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
AU$158
Highest Price
AU$548
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 AU$273 per night from 8 Apr to 9 Apr
AU$273
includes taxes & fees
8 Apr - 9 Apr
With a stay at Wilder House Berkshires in Sheffield, you'll be within a 5-minute drive of Lime Kiln Farm Wildlife Sanctuary and Thom Reed UFO Monument Park.
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 AU$171 per night from 17 Apr to 18 Apr
AU$171
includes taxes & fees
17 Apr - 18 Apr
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
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 AU$158 per night from 13 Apr to 14 Apr
AU$158
includes taxes & fees
13 Apr - 14 Apr
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
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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 refundable
The price is AU$232 per night from 8 Apr to 9 Apr
AU$232
includes taxes & fees
8 Apr - 9 Apr
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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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.