Book Holiday Homes in Cheshire

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Featured Holiday Homes in Cheshire

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$361 per night from 17 Apr to 18 Apr
AU$361
includes taxes & fees
17 Apr - 18 Apr
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
The price is AU$1,655 per night from 5 Apr to 6 Apr
AU$1,655
includes taxes & fees
5 Apr - 6 Apr
With a stay at this vacation home in Pittsfield, you'll be on the waterfront, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Hancock Village Inn at Jiminy Peak
1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Shelburne Falls
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
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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
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!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

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

Richmond
With a stay at this vacation home in Richmond, you'll be within a 10-minute drive of Tanglewood Music Center and Fairfield Brook WMA.
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home

Mountain Blossom Retreat by Evergreen Home

Lanesborough
With a stay at this vacation home in Lanesborough, you'll be in the mountains, within a 15-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State ...
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Becket
When you stay at this vacation home in Becket, you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Quintessential 6-BR Berkshires Lodge
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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.

Cheshire 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 Cheshire vacation homes are the perfect way for you to wing it.

Holiday houses in Cheshire 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 Cheshire 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 Cheshire adventures, obvs.

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

Cheshire Holiday Homes essential information

Accommodation
288 Holiday Homes
Lowest Price
AU$158
Highest Price
AU$1,655
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Hancock Village Inn at Jiminy Peak, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Peace and quiet on the lake, Heart of Lenox Walk to Town Cozy Cottage!, Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!, Mountain Blossom Retreat by Evergreen Home, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Quintessential 6-BR Berkshires Lodge

Top trending hotels in Cheshire

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
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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The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$379 per night from 6 Apr to 7 Apr
AU$379
includes taxes & fees
6 Apr - 7 Apr
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
The Williams Inn
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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.