Cheshire, MA vacation rentals

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229 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Cheshire, MA

Jiminy Peak Mountain Resort - Cheshire, MA
8.4Very good 1939 reviews
Cheshire, MA
4 3
$349/nighttotal: $698 (2 )

Jiminy Peak Mountain Resort

resort - Hancock
Jiminy Peak Mountain Resort is a family-friendly resort located in the scenic mountains of Hancock, just 0.1 mi from Jiminy Peak Mountain Resort. It offers ski-in/ski-out access, a private pool, and a fireplace.
With a user rating of "very good" and an excellent location and cleanliness rating, Jiminy Peak Mountain Resort is a popular choice for travelers visiting Hancock.
The resort features a fully equipped kitchen, a TV with a DVD player, a sofa bed, a refrigerator, a microwave, and a stovetop. Guests can also enjoy access to the fitness center and the smoke-free environment.
Large Secluded Berkshire Home - Cheshire, MA
9.6Excellent 144 reviews
Cheshire, MA
4 3
$639/nighttotal: $1278 (2 )

Large Secluded Berkshire Home

apartment - Cheshire
Apartment to rent for up to 10 people with an excellent rating of 96% based on 144 reviews. You will be located in Cheshire.
Facilities and services: a freeze, a kitchen and free parking. This apartment in Cheshire also has a garden!
Cozy Home Located In The Berkshires! Pet Friendly With Fenced Yard. - Cheshire, MA
10Excellent 180 reviews
Cheshire, MA
4 2
$317/nighttotal: $634 (2 )

Cozy Home Located In The Berkshires! Pet Friendly With Fenced Yard.

house - Adams
House rental listing with an excellent rating of 100% based on 180 reviews. This accommodation is located in Adams.
Facilities and services: a barbecue, a kitchen and a dish washer. You can bring your favorite pets this house!
Vacation Village In The Berkshires - Cheshire, MA
8.6Very good 2748 reviews
Cheshire, MA
4 1
$256/nighttotal: $512 (2 )

Vacation Village In The Berkshires

resort - Hancock
Located in the scenic Berkshires, Vacation Village is a pet-friendly resort near Jiminy Peak Mountain Ski Resort. It has very good user and location ratings and excellent cleanliness ratings.
The resort offers a variety of amenities, including a state-of-the-art fitness center, private balconies and patios, fully and partially equipped kitchens, a swimming pool, a Jacuzzi, a terrace, a garden, a spa, a concierge, a tennis court and parking.
Guests can enjoy convenient access to outdoor activities such as biking, skiing, fishing and swimming, as well as historical sites and dining options.
Berkshire County Post-and-beam Barn! - Cheshire, MA
9.9Excellent 59 reviews
Cheshire, MA
4 3
$685/nighttotal: $1370 (2 )

Berkshire County Post-and-beam Barn!

apartment - Cheshire
Apartment rental listing for 10 guests with an excellent rating of 99% based on 59 reviews. You will be in Cheshire.
Facilities and services include free parking, air conditioning and a garden.
*Berkshire's Sweet Spot-close To Ski Resorts/spa - Cheshire, MA
9.9Excellent 59 reviews
Cheshire, MA
4 3
$357/nighttotal: $714 (2 )

*Berkshire's Sweet Spot-close To Ski Resorts/spa

apartment - Pittsfield
This 3-bedroom apartment is located in Central Berkshire County, within walking distance to downtown Pittsfield. It is close to attractions such as Tanglewood, Mass MoCA and Lenox, and surrounded by public lakes and hiking trails.
The apartment has an excellent user, location and cleanliness rating. It can accommodate up to 8 guests and has 1 bathroom.
The apartment features a fully equipped kitchen, air conditioning, a seasonal in-ground pool, a year-round spa, a garden, parking, a cozy porch, and is fully furnished with linens, towels, and basic toiletries.
Berkshire Lake Access - Cheshire, MA
10Excellent 41 reviews
Cheshire, MA
4 4
$343/nighttotal: $686 (2 )

Berkshire Lake Access

apartment - Hinsdale
Apartment rental from 218 dollars for 6 people with an excellent rating of 100% based on 41 reviews. This accommodation is located in Hinsdale.
Services and facilities: a kitchen, a fridge and a washing machine. Take advantage of the air conditioning in this apartment!
Sheep Barn On The Greylock Valley Estate - Cheshire, MA
9.8Excellent 215 reviews
Cheshire, MA
4 3
$337/nighttotal: $674 (2 )

Sheep Barn On The Greylock Valley Estate

gîte - New Ashford
Gîte listing for 6 people with an excellent rating of 98% based on 215 reviews. This accommodation is located in New Ashford.
Facilities and services: a barbecue, free parking and an iron. Pets are welcome in this accommodation.
Marie's Place - Cheshire, MA
9.8Excellent 218 reviews
Cheshire, MA
4 1
$193/nighttotal: $386 (2 )

Marie's Place

apartment - Pittsfield
This apartment is located in the city center of Pittsfield, near the Berkshire Museum, the Colonial Theater, and the Barrington Stage Company. The location is excellent, with a user rating of excellent and a cleanliness rating of excellent.
The apartment has two bedrooms with queen-size beds and can accommodate up to 4 guests. It has a fully furnished kitchen, dining room, and living room, as well as an enclosed porch for relaxation. The apartment also has on-site laundry and off-street parking.
*Berkshire's Sweet Spot 2-close To Ski Resorts/spa - Cheshire, MA
9.7Excellent 59 reviews
Cheshire, MA
4 1
$343/nighttotal: $686 (2 )

*Berkshire's Sweet Spot 2-close To Ski Resorts/spa

apartment - Pittsfield
This apartment is located in Pittsfield, in a peaceful residential area, within walking distance of the city center and popular landmarks. It has received excellent ratings for its location, cleanliness, and amenities.
The apartment has one bathroom and can accommodate up to 8 guests. It features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a jacuzzi, a garden, and parking. Guests can also enjoy nearby activities such as hiking, biking, and fishing.
Bear Minimum - Cheshire, MA
9.9Excellent 69 reviews
Cheshire, MA
4 2
$286/nighttotal: $572 (2 )

Bear Minimum

apartment - Savoy
Apartment for 6 people with an excellent rating of 99% based on 69 reviews. This accommodation is based in Savoy.
Services and facilities include a freeze, a coffee place and a barbecue. This apartment in Savoy also has a garden!
Hearts Desire Is A Furnished Whole House In A Small, Colorful Garden Center. - Cheshire, MA
10Excellent 128 reviews
Cheshire, MA
4 3
$326/nighttotal: $652 (2 )

Hearts Desire Is A Furnished Whole House In A Small, Colorful Garden Center.

house - Lanesborough
This house is situated on a lake in Lanesborough, within 10 km of Mount Greylock State Reservation and Jiminy Peak Mountain Resort. It has an excellent user rating.
The house has 3 bedrooms, 1 bathroom, and can accommodate up to 6 guests.
It features a fully equipped kitchen, a spa tub, a fireplace, a barbecue grill, a garden, a terrace/balcony, air conditioning, internet, parking, and it's pet-friendly.
The unique lakeside location, the proximity to landmarks, and the amenities make this house an appealing choice for travelers visiting Lanesborough.

Best Cheshire, MA vacation rentals with a pool

Among the 229 accommodations in Cheshire, MA, here are the 8 best rentals with a pool

Berkshire Family Getaway At Jiminy Peak! - Cheshire, MA
9.9Excellent 70 reviews
Cheshire, MA
4 4
$642/nighttotal: $1284 (2 )

Berkshire Family Getaway At Jiminy Peak!

house - Hancock
Vacation house rental for up to 12 guests with an excellent rating of 99% based on 70 reviews. You will stay in Hancock.
Services and facilities include a fridge, an iron and an access for persons with reduced mobility. Take advantage of the jacuzzi in this house.
Vicinu A Muntagna, A Home Near The Mountain - Cheshire, MA
10Excellent 37 reviews
Cheshire, MA
4 4
$804/nighttotal: $1608 (2 )

Vicinu A Muntagna, A Home Near The Mountain

house - Hancock
House rental listing for 12 people with an excellent rating of 100% based on 37 reviews. This accommodation is based in Hancock.
Facilities and services include a coffee place, a swimming pool and a washing machine. You can also relax in the jacuzzi!
Private & Stylish Berkshires House For All Seasons - Cheshire, MA
9.8Excellent 79 reviews
Cheshire, MA
4 4
$594/nighttotal: $1188 (2 )

Private & Stylish Berkshires House For All Seasons

apartment - Dalton
Accommodation for 8 guests with an excellent rating of 98% based on 79 reviews. You will be based in Dalton.
Services and facilities: a garden, free parking and a kitchen. This apartment is ideal for families.
Berkshire County Modern Home + Pool - Cheshire, MA
9.9Excellent 50 reviews
Cheshire, MA
4 4
$685/nighttotal: $1370 (2 )

Berkshire County Modern Home + Pool

- Cheshire
Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn - Cheshire, MA
9.7Excellent 34 reviews
Cheshire, MA
4 1
$415/nighttotal: $830 (2 )

Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

apartment - Hancock
This apartment is located in the mountains of Hancock, within easy reach of Jiminy Peak Mountain Resort (0.1 mi). It has an excellent user rating.
The apartment has 1 bedroom, 1 bathroom, and a floor area of 500 square feet. It can accommodate up to 4 guests.
The apartment features a well-equipped kitchen, a cozy fireplace, a TV with a DVD player, and a sofa bed for additional sleeping arrangements. It also has access to an indoor pool, a fitness center, and a swimming pool. Guests can also enjoy ski-in/ski-out access for winter sports.
Ski On Ski Off 1 Br Loft Condo In The Village Center With Private Gated Parking - Cheshire, MA
10Excellent 26 reviews
Cheshire, MA
4 1
$837/nighttotal: $1674 (2 )

Ski On Ski Off 1 Br Loft Condo In The Village Center With Private Gated Parking

apartment - Hancock
This mountain condo is located near Jiminy Peak Mountain Resort, Mount Greylock State Reservation Visitor Center, and Brodie Mountain. It has excellent user ratings.
The apartment has one bedroom, one bathroom, and can accommodate up to four guests.
It features a fully equipped kitchen, a fireplace, a sofa bed, a smart TV, a washing machine, and a dryer. Guests can also enjoy access to an indoor and outdoor pool, a fitness center, a tennis court, and parking.
Unique - Themed Country Suite @ Jiminy Peak - Cheshire, MA
9.9Excellent 28 reviews
Cheshire, MA
4 1
$324/nighttotal: $648 (2 )

Unique - Themed Country Suite @ Jiminy Peak

apartment - Hancock
Apartment for 6 guests with an excellent rating of 99% based on 28 reviews. You will be based in Hancock.
Facilities and services include an access for persons with reduced mobility, a freeze and an iron. Enjoy a gym in this apartment in Hancock!
Newly Renovated Mountainside Townhome, Jiminy Peak - Cheshire, MA
9.7Excellent 13 reviews
Cheshire, MA
4 2
$485/nighttotal: $970 (2 )

Newly Renovated Mountainside Townhome, Jiminy Peak

house - Hancock
Book this vacation rental for 6 guests with an excellent rating of 97% based on 13 reviews. Your accommodation will be based in Hancock.
Services and facilities include a dish washer, a garden and a sauna. This house in Hancock has a swimming pool!

Best family friendly Cheshire, MA vacation rentals

Among the 229 accommodations in Cheshire, MA, here are the 8 best family friendly rentals

Ashmere Lake Log Cabin With Privacy \/ 2 Bedrooms - Cheshire, MA
9.7Excellent 52 reviews
Cheshire, MA
4 2
$352/nighttotal: $704 (2 )

Ashmere Lake Log Cabin With Privacy \/ 2 Bedrooms

cabin - Hinsdale
Cabin rental from 199 dollars for up to 4 people with an excellent rating of 97% based on 52 reviews. You will be located in Hinsdale.
Services and facilities: a washing machine, free parking and a dish washer. This accommodation also has a terrace!
Cleveland House - Renovated Berkshires' Gem. - Cheshire, MA
10Excellent 117 reviews
Cheshire, MA
4 6
$628/nighttotal: $1256 (2 )

Cleveland House - Renovated Berkshires' Gem.

- Dalton
Peaceful Family Home W/ Fire Pit & Large Yard - Cheshire, MA
10Excellent 30 reviews
Cheshire, MA
4 3
$583/nighttotal: $1166 (2 )

Peaceful Family Home W/ Fire Pit & Large Yard

house - Williamstown
House for 6 people with an excellent rating of 100% based on 30 reviews. You will be located in Williamstown.
Facilities and services: an iron, a jacuzzi and a dish washer. Take advantage of the garden in this house in Williamstown.
Central Berkshire Bungalow By Evergreen Home - Cheshire, MA
9.9Excellent 36 reviews
Cheshire, MA
4 2
$375/nighttotal: $750 (2 )

Central Berkshire Bungalow By Evergreen Home

apartment - Pittsfield
This charming apartment is located in a quiet residential area within walking distance of the city center. It is close to Tanglewood, Barrington Stage Company, and other cultural attractions.
This apartment has excellent user, cleanliness, and location ratings.
It has 2 bedrooms, 2 bathrooms, and can accommodate up to 5 guests. It has a floor area of 1090 square feet.
This apartment is fully equipped and features a kitchen, a separate dining room, air conditioning, free WiFi, and a garden. It also has a deck for outdoor dining, a large flat-screen TV, and is pet-friendly.
Cozy Berkshire Cottage With Fireplace. - Cheshire, MA
10Excellent 40 reviews
Cheshire, MA
4 3
$338/nighttotal: $676 (2 )

Cozy Berkshire Cottage With Fireplace.

cottage - Pittsfield
This cottage is located in the heart of Pittsfield, within easy reach of the Housatonic River and cultural landmarks such as the Colonial Theater. It has an excellent user rating.
With 980 square feet of floor area, this cottage can accommodate up to 5 guests in its 3 bedrooms and 2 bathrooms.
Guests can enjoy a secluded mountain setting with picturesque views, a garden, barbecue grills, a cozy interior with a fireplace, a fully equipped kitchen, free WiFi, and a private patio.
Peaceful Family Home With Fire Pit And Large Yard - Cheshire, MA
Cheshire, MA
4 1
$569/nighttotal: $1138 (2 )

Peaceful Family Home With Fire Pit And Large Yard

house - Williamstown
Vacation rental listing. Your accommodation will be located in Williamstown.
Services and facilities: a kitchen, air conditioning and a fridge. Take advantage of the Free Parking with this accommodation in Williamstown!
Unique - 1br Country Condo @ Jiminy Peak - Cheshire, MA
10Excellent 16 reviews
Cheshire, MA
4 1
$465/nighttotal: $930 (2 )

Unique - 1br Country Condo @ Jiminy Peak

apartment - Hancock
Vacation rental listing with an excellent rating of 100% based on 16 reviews. You will be based in Hancock.
Services and facilities include a child space, a kitchen and a fitness center. Enjoy a swimming pool in this apartment in Hancock!
Beautiful Apartment In Central Pittsfield - Cheshire, MA
9.3Excellent 40 reviews
Cheshire, MA
4 2
$250/nighttotal: $500 (2 )

Beautiful Apartment In Central Pittsfield

apartment - Pittsfield
This charming apartment is located in Downtown Pittsfield, just 3 minutes away from Lake Onota. You'll enjoy the historic ambiance of this 1840s home while taking advantage of its modern amenities.
With excellent user, location, and cleanliness ratings, this apartment offers a comfortable stay for up to 5 guests in its 2 bedrooms and 1 bathroom.
The open concept living area includes a fully equipped kitchen and a washer/dryer for your convenience. The large fenced-in backyard is perfect for outdoor relaxation, and the bonus finished attic provides extra space for yoga or sleeping. Off-street parking and contactless check-in add to the convenience of your stay. Spanish-speaking staff is also available for assistance.

Frequently asked questions for the vacation rentals in Cheshire, MA

Destinations nearby

Best pet friendly Cheshire, MA vacation rentals

Among the 229 accommodations in Cheshire, MA, here are the 8 best pet friendly rentals

The Inn At Berkshire Farm Sanctuary - Cheshire, MA
9.9Excellent 37 reviews
Cheshire, MA
4 3
$656/nighttotal: $1312 (2 )

The Inn At Berkshire Farm Sanctuary

gîte - Peru
Gîte listing for up to 6 guests with an excellent rating of 99% based on 37 reviews. You will be located in Peru.
Facilities and services include a washing machine, a coffee place and an iron. You can bring your favorite pets this accommodation!
Country Living Just Minutes From Everything! - Cheshire, MA
10Excellent 44 reviews
Cheshire, MA
4 3
$633/nighttotal: $1266 (2 )

Country Living Just Minutes From Everything!

house - Pittsfield
This house is located in the mountains, 3.1 miles from Hancock Shaker Village, near Pleasant Valley Wilderness Sanctuary, Bousquet Ski Area, Lenox Mountain, and Guido's Marketplace. It has an excellent user rating.
The house has 3 bedrooms, 2 bathrooms, and a floor area of 1850 square feet. It can accommodate up to 8 guests.
The house has a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a terrace/balcony, a garden, a spa, a fitness center, and parking. Guests can enjoy stunning views of the mountains and access to a fitness center, garden, and barbecue grills.
Mount Greylock View Retreat,3 Bedroom,2 1/2 Bath - Cheshire, MA
9.8Excellent 38 reviews
Cheshire, MA
4 3
$399/nighttotal: $798 (2 )

Mount Greylock View Retreat,3 Bedroom,2 1/2 Bath

- Adams
Art House! Spacious Getaway By Mass Moca - Cheshire, MA
9.8Excellent 105 reviews
Cheshire, MA
4 6
$741/nighttotal: $1482 (2 )

Art House! Spacious Getaway By Mass Moca

house - North Adams
House listing for up to 12 guests with an excellent rating of 98% based on 105 reviews. Your accommodation will be based in North Adams.
Services and facilities include a dish washer, a coffee place and a terrace. You can bring your favorite pets this house!
Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous - Cheshire, MA
9.9Excellent 32 reviews
Cheshire, MA
4 2
$676/nighttotal: $1352 (2 )

Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous

apartment - Hancock
Apartment listing with an excellent rating of 99% based on 32 reviews. Your accommodation will be located in Hancock.
Services and facilities: a swimming pool, a washing machine and a jacuzzi. Take advantage of the gym in this apartment in Hancock.
Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat - Cheshire, MA
9.8Excellent 28 reviews
Cheshire, MA
4 1
$415/nighttotal: $830 (2 )

Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

apartment - Hancock
Apartment listing with an excellent rating of 98% based on 28 reviews. You will be based in Hancock.
Facilities and services include an elevator, a fridge and an iron. Enjoy a gym in this apartment in Hancock!
Gorgeous Zen Must-see Suite At Jiminy Country Inn - Sleeps 4 Ski On/off At Mtn - Cheshire, MA
9.4Excellent 30 reviews
Cheshire, MA
4 1
$477/nighttotal: $954 (2 )

Gorgeous Zen Must-see Suite At Jiminy Country Inn - Sleeps 4 Ski On/off At Mtn

apartment - Hancock
Apartment listing with an excellent rating of 94% based on 30 reviews. You will stay in Hancock.
Services and facilities: a jacuzzi, a fitness center and an iron. This apartment is ideal for families.
Cozy Cabin In Resort In Cultural Berkshire County - Cheshire, MA
10Excellent 19 reviews
Cheshire, MA
4 2
$457/nighttotal: $914 (2 )

Cozy Cabin In Resort In Cultural Berkshire County

apartment - Hancock
Apartment for 5 guests with an excellent rating of 100% based on 19 reviews. This accommodation is located in Hancock.
Services and facilities: a fridge, air conditioning and free parking. You can also relax in the jacuzzi!