Search Vacation Homes in Cheshire

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Vacation Homes in Cheshire

Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Dec 8 - Dec 9
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
$330 nightly
The price is $370
Dec 4 - Dec 5
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$316 nightly
The price is $339
Dec 4 - Dec 5
Total with taxes and fees
Florida Mountain Log Cabin
Fridge, microwave, oven, stovetop
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Whitingham
10.0 out of 10, Exceptional, (14)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
$474 nightly
The price is $531
Dec 9 - Dec 10
Total with taxes and fees
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Fridge, microwave, oven, stovetop
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Bennington
8.6 out of 10, Excellent, (34)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
United States
Ransom W.
$256 nightly
The price is $272
Dec 14 - Dec 15
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.2 out of 10, Wonderful, (24)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
$404 nightly
The price is $451
Dec 4 - Dec 5
Total with taxes and fees
North Getaway Cottage
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$441 nightly
The price is $493
Dec 5 - Dec 6
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop
The Greylock Cabin

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
$405 nightly
The price is $437
Dec 8 - Dec 9
Total with taxes and fees
The Greylock Cabin
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
$352 nightly
The price is $393
Dec 10 - Dec 11
Total with taxes and fees
Riverbend Berkshire East Basecamp - 3 bedrooms available
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
$490 nightly
The price is $547
Dec 4 - Dec 5
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Panoramic House | Private kitchen
Two Brooks Lodge

Two Brooks Lodge

3.0 star property
Bennington
4.8 out of 10, (3)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
$240 nightly
The price is $250
Dec 14 - Dec 15
Total with taxes and fees
Two Brooks Lodge
Outdoor dining
Charlemont Chalet - A 15 Acre Private Retreat

Charlemont Chalet - A 15 Acre Private Retreat

2.0 star property
Charlemont
$614 nightly
The price is $662
Dec 15 - Dec 16
Total with taxes and fees
Charlemont Chalet - A 15 Acre Private Retreat
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
$666 nightly
The price is $743
Dec 10 - Dec 11
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
$722 nightly
The price is $733
Dec 4 - Dec 5
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
Interior
Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham

Old Chatham
$421 nightly
The price is $472
Dec 4 - Dec 5
Total with taxes and fees
Artists’ Hideaway in Old Chatham
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,026 nightly
The price is $1,111
Dec 9 - Dec 10
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Cheshire

Cheshire Vacation Homes information

Number of reviews
Accommodation
281 Vacation Homes
Lowest Price
$250
Highest Price
$250

Explore a world of travel with Expedia