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 30 Dec to 31 Dec
AU$361
includes taxes & fees
30 Dec - 31 Dec
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!!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham
Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
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
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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
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.
Amore Estate - beautiful room with many places to explore and relax in.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox
Located in Lenox, this vacation home is within a 15-minute walk of Pleasant Valley Wilderness Sanctuary and Kennedy Park.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

Stockbridge
A stay at this vacation home places you in the heart of Stockbridge, steps from Housatonic River and Mission House.
A Grand property in Historic Stockbridge
Charlemont Retreat on Chickley River w/ EV Charger

Charlemont Retreat on Chickley River w/ EV Charger

Hawley
Located in Charlemont, this vacation home is in a rural location, within a 15-minute drive of Mohawk Trail State Forest and Zoar Outdoor/Deerfield Valley Canopy ...
Charlemont Retreat on Chickley River w/ EV Charger
Berkshire Ashmere Lake lodging. Quiet  room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
With a stay at this vacation home in Hinsdale, you'll be within a 15-minute drive of Bas Ridge Golf Course and Crane Museum of Papermaking.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
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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
231 Holiday Homes
Lowest Price
AU$158
Highest Price
AU$361
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating , Peace and quiet on the lake, Quintessential 6-BR Berkshires Lodge, Amore Estate - beautiful room with many places to explore and relax in., Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, A Grand property in Historic Stockbridge, Charlemont Retreat on Chickley River w/ EV Charger, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Top trending hotels in Cheshire

Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 5 Jan to 6 Jan
AU$207
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at Hotel Downstreet places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot from Massachusetts Museum ...
Hotel Downstreet
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$173 per night from 30 Dec to 31 Dec
AU$173
includes taxes & fees
30 Dec - 31 Dec
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
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$158 per night from 1 Jan to 2 Jan
AU$158
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
Life House Berkshires
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The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$360 per night from 5 Jan to 6 Jan
AU$360
includes taxes & fees
5 Jan - 6 Jan 2025
When you a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 5-minute walk of Housatonic River and Mission House.
The Red Lion 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.