We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cheshire Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Cheshire.
19th c. Barn in the Berkshires, vacation rental in Cheshire
19th c. Barn in the Berkshires, vacation rental in Cheshire
19th c. Barn in the Berkshires, vacation rental in Cheshire

19th c. Barn in the Berkshires

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Berkshires Lakefront Retreat on 4 Private Acres, vacation rental in Cheshire
Berkshires Lakefront Retreat on 4 Private Acres, vacation rental in Cheshire
Berkshires Lakefront Retreat on 4 Private Acres, vacation rental in Cheshire

Berkshires Lakefront Retreat on 4 Private Acres

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The following properties within 20 miles of Cheshire match all your filters:
Cozy Rustic suite in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak, vacation rental in Cheshire
Cozy Rustic suite in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak, vacation rental in Cheshire
Cozy Rustic suite in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak, vacation rental in Cheshire

Cozy Rustic suite in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Berkshire Village Carriage House - Super Private!!, vacation rental in Cheshire
Berkshire Village Carriage House - Super Private!!, vacation rental in Cheshire
Berkshire Village Carriage House - Super Private!!, vacation rental in Cheshire

Berkshire Village Carriage House - Super Private!!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Hearts Desire is a furnished whole house in a small, colorful garden center., vacation rental in Cheshire
Hearts Desire is a furnished whole house in a small, colorful garden center., vacation rental in Cheshire
Hearts Desire is a furnished whole house in a small, colorful garden center., vacation rental in Cheshire

Hearts Desire is a furnished whole house in a small, colorful garden center.

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming Suite in 18th c. Berkshire Farmhouse near Mt.Greylock and Jiminy Peak, vacation rental in Cheshire
Charming Suite in 18th c. Berkshire Farmhouse near Mt.Greylock and Jiminy Peak, vacation rental in Cheshire
Charming Suite in 18th c. Berkshire Farmhouse near Mt.Greylock and Jiminy Peak, vacation rental in Cheshire

Charming Suite in 18th c. Berkshire Farmhouse near Mt.Greylock and Jiminy Peak

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo, vacation rental in Cheshire
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo, vacation rental in Cheshire
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo, vacation rental in Cheshire

Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Bright Boho Suite in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak, vacation rental in Cheshire
Bright Boho Suite in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak, vacation rental in Cheshire
Bright Boho Suite in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak, vacation rental in Cheshire

Bright Boho Suite in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2, vacation rental in Cheshire
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2, vacation rental in Cheshire
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2, vacation rental in Cheshire

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy home located in The Berkshires! PET FRIENDLY with fenced yard., vacation rental in Cheshire
Cozy home located in The Berkshires! PET FRIENDLY with fenced yard., vacation rental in Cheshire
Cozy home located in The Berkshires! PET FRIENDLY with fenced yard., vacation rental in Cheshire

Cozy home located in The Berkshires! PET FRIENDLY with fenced yard.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in Cheshire
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in Cheshire
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in Cheshire

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, vacation rental in Cheshire
A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, vacation rental in Cheshire
A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, vacation rental in Cheshire

A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming historic cottage on scenic road to Mt. Greylock, vacation rental in Cheshire
Charming historic cottage on scenic road to Mt. Greylock, vacation rental in Cheshire
Charming historic cottage on scenic road to Mt. Greylock, vacation rental in Cheshire

Charming historic cottage on scenic road to Mt. Greylock

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
6-BR Country Estate 14-Min. to Jiminy Peak, vacation rental in Cheshire
6-BR Country Estate 14-Min. to Jiminy Peak, vacation rental in Cheshire
6-BR Country Estate 14-Min. to Jiminy Peak, vacation rental in Cheshire

6-BR Country Estate 14-Min. to Jiminy Peak

Rental Home
6 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in Cheshire
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in Cheshire
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation rental in Cheshire

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Mountain living, Hot Tub, 1 bedroom apartment, vacation rental in Cheshire
Mountain living, Hot Tub, 1 bedroom apartment, vacation rental in Cheshire
Mountain living, Hot Tub, 1 bedroom apartment, vacation rental in Cheshire

Mountain living, Hot Tub, 1 bedroom apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Family-Friendly Hancock Home: Walk to Slopes!, vacation rental in Cheshire
Family-Friendly Hancock Home: Walk to Slopes!, vacation rental in Cheshire
Family-Friendly Hancock Home: Walk to Slopes!, vacation rental in Cheshire

Family-Friendly Hancock Home: Walk to Slopes!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Available for Healthcare and long term stays welcome 3 miles from Hospital, vacation rental in Cheshire
Available for Healthcare and long term stays welcome 3 miles from Hospital, vacation rental in Cheshire
Available for Healthcare and long term stays welcome 3 miles from Hospital, vacation rental in Cheshire

Available for Healthcare and long term stays welcome 3 miles from Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Monthly/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA, vacation rental in Cheshire
Monthly/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA, vacation rental in Cheshire
Monthly/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA, vacation rental in Cheshire

Monthly/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Park Street Penthouse Apartment, vacation rental in Cheshire
Park Street Penthouse Apartment, vacation rental in Cheshire
Park Street Penthouse Apartment, vacation rental in Cheshire

Park Street Penthouse Apartment

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Mounatin Getaway in the Heart of the Berkshires!, vacation rental in Cheshire
Mounatin Getaway in the Heart of the Berkshires!, vacation rental in Cheshire
Mounatin Getaway in the Heart of the Berkshires!, vacation rental in Cheshire

Mounatin Getaway in the Heart of the Berkshires!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Available for Winter Rental, Healthcare, Central, vacation rental in Cheshire
Available for Winter Rental, Healthcare, Central, vacation rental in Cheshire
Available for Winter Rental, Healthcare, Central, vacation rental in Cheshire

Available for Winter Rental, Healthcare, Central

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Ski Jiminy New Year's Eve, vacation rental in Cheshire
Ski Jiminy New Year's Eve, vacation rental in Cheshire
Ski Jiminy New Year's Eve, vacation rental in Cheshire

Ski Jiminy New Year's Eve

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Historic Stone Church in The Berkshires, vacation rental in Cheshire
Historic Stone Church in The Berkshires, vacation rental in Cheshire
Historic Stone Church in The Berkshires, vacation rental in Cheshire

Historic Stone Church in The Berkshires

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Wyndham Bentley Brook Condo Resort, vacation rental in Cheshire
Wyndham Bentley Brook Condo Resort, vacation rental in Cheshire
Wyndham Bentley Brook Condo Resort, vacation rental in Cheshire

Wyndham Bentley Brook Condo Resort

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cheshire
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cheshire
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Cheshire

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!, vacation rental in Cheshire
2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!, vacation rental in Cheshire
2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!, vacation rental in Cheshire

2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!, vacation rental in Cheshire
2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!, vacation rental in Cheshire
2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!, vacation rental in Cheshire

2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Private and Cheerful Berkshire Oasis in Dalton with in-ground pool, vacation rental in Cheshire
Private and Cheerful Berkshire Oasis in Dalton with in-ground pool, vacation rental in Cheshire
Private and Cheerful Berkshire Oasis in Dalton with in-ground pool, vacation rental in Cheshire

Private and Cheerful Berkshire Oasis in Dalton with in-ground pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lakeside Berkshires Home Near Hiking & Skiing!, vacation rental in Cheshire
Lakeside Berkshires Home Near Hiking & Skiing!, vacation rental in Cheshire
Lakeside Berkshires Home Near Hiking & Skiing!, vacation rental in Cheshire

Lakeside Berkshires Home Near Hiking & Skiing!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Bright and Sunny Ranch with Hot Tub & Lake Access!, vacation rental in Cheshire
Bright and Sunny Ranch with Hot Tub & Lake Access!, vacation rental in Cheshire
Bright and Sunny Ranch with Hot Tub & Lake Access!, vacation rental in Cheshire

Bright and Sunny Ranch with Hot Tub & Lake Access!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Wildlife Cottage by the Lake, vacation rental in Cheshire
Wildlife Cottage by the Lake, vacation rental in Cheshire
Wildlife Cottage by the Lake, vacation rental in Cheshire

Wildlife Cottage by the Lake

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy Berkshire Home with Spectacular views!
3 bedrooms/2 baths  ~ Sleeps 6, vacation rental in Cheshire
Cozy Berkshire Home with Spectacular views!
3 bedrooms/2 baths  ~ Sleeps 6, vacation rental in Cheshire
Cozy Berkshire Home with Spectacular views!
3 bedrooms/2 baths  ~ Sleeps 6, vacation rental in Cheshire

Cozy Berkshire Home with Spectacular views! 3 bedrooms/2 baths ~ Sleeps 6

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Stylish Berkshire Haven; Mountain Views, 3 Acres, vacation rental in Cheshire
Stylish Berkshire Haven; Mountain Views, 3 Acres, vacation rental in Cheshire
Stylish Berkshire Haven; Mountain Views, 3 Acres, vacation rental in Cheshire

Stylish Berkshire Haven; Mountain Views, 3 Acres

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Huge Beautiful House-2 families-16 Acres -Low rate March 3-5/ 2 min from Jiminy, vacation rental in Cheshire
Huge Beautiful House-2 families-16 Acres -Low rate March 3-5/ 2 min from Jiminy, vacation rental in Cheshire
Huge Beautiful House-2 families-16 Acres -Low rate March 3-5/ 2 min from Jiminy, vacation rental in Cheshire

Huge Beautiful House-2 families-16 Acres -Low rate March 3-5/ 2 min from Jiminy

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in Cheshire
Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in Cheshire
Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in Cheshire

Jiminy Peak Mountainside Getaway in the Berkshires

Condo/Apartment
3 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Cheshire
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Cheshire
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Cheshire

Mountainside: Large 3-level Jiminy Peak Home

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Berkshire Lake House vacation home, vacation rental in Cheshire
Berkshire Lake House vacation home, vacation rental in Cheshire
Berkshire Lake House vacation home, vacation rental in Cheshire

Berkshire Lake House vacation home

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!, vacation rental in Cheshire
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!, vacation rental in Cheshire
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!, vacation rental in Cheshire

Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, vacation rental in Cheshire
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, vacation rental in Cheshire
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, vacation rental in Cheshire

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Family-friendly home, in town - walk to dining & more! Fireplace, patio, views!, vacation rental in Cheshire
Family-friendly home, in town - walk to dining & more! Fireplace, patio, views!, vacation rental in Cheshire
Family-friendly home, in town - walk to dining & more! Fireplace, patio, views!, vacation rental in Cheshire

Family-friendly home, in town - walk to dining & more! Fireplace, patio, views!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak., vacation rental in Cheshire
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak., vacation rental in Cheshire
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak., vacation rental in Cheshire

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful Home away from Home, vacation rental in Cheshire
Beautiful Home away from Home, vacation rental in Cheshire
Beautiful Home away from Home, vacation rental in Cheshire

Beautiful Home away from Home

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Jiminy Peak, Berskshires, MA, Luxe Living, vacation rental in Cheshire
Jiminy Peak, Berskshires, MA, Luxe Living, vacation rental in Cheshire
Jiminy Peak, Berskshires, MA, Luxe Living, vacation rental in Cheshire

Jiminy Peak, Berskshires, MA, Luxe Living

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Family Friendly Townhouse in the Heart of Jiminy Peak, vacation rental in Cheshire
Family Friendly Townhouse in the Heart of Jiminy Peak, vacation rental in Cheshire
Family Friendly Townhouse in the Heart of Jiminy Peak, vacation rental in Cheshire

Family Friendly Townhouse in the Heart of Jiminy Peak

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Brooksong, the perfect Berkshires getaway, vacation rental in Cheshire
Brooksong, the perfect Berkshires getaway, vacation rental in Cheshire
Brooksong, the perfect Berkshires getaway, vacation rental in Cheshire

Brooksong, the perfect Berkshires getaway

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Elegant house nestled in the scenic hills of Northern Berkshire County., vacation rental in Cheshire
Elegant house nestled in the scenic hills of Northern Berkshire County., vacation rental in Cheshire
Elegant house nestled in the scenic hills of Northern Berkshire County., vacation rental in Cheshire

Elegant house nestled in the scenic hills of Northern Berkshire County.

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
6BR Berkshire Bliss - 38 private acres - close to skiing and town, vacation rental in Cheshire
6BR Berkshire Bliss - 38 private acres - close to skiing and town, vacation rental in Cheshire
6BR Berkshire Bliss - 38 private acres - close to skiing and town, vacation rental in Cheshire

6BR Berkshire Bliss - 38 private acres - close to skiing and town

Rental Home
6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, vacation rental in Cheshire
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, vacation rental in Cheshire
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, vacation rental in Cheshire

6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort

Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Thanksgiving week lux condo/4 Berkshires, vacation rental in Cheshire
Thanksgiving week lux condo/4 Berkshires, vacation rental in Cheshire
Thanksgiving week lux condo/4 Berkshires, vacation rental in Cheshire

Thanksgiving week lux condo/4 Berkshires

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Showing results 1-50 of 50
Frequently Asked Questions about Cheshire