Cheshire Vacation Rentals

Compare 440 available properties from 19 providers
Cheshire
Save up to 26%

Best Vacation Home Deals in Cheshire

-20%
House ∙ 6 guests ∙ 3 bedrooms
Williamstown, Berkshire County, Massachusetts, United States
from $279 $349
VRBO
4.0
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-26%
House ∙ 4 guests ∙ 2 bedrooms
Hinsdale, Berkshire County, Massachusetts, United States
from $102 $137
VRBO
4.6
View deal

Discover a vacation rental matching your needs among the 440 beautiful rentals from several providers in Cheshire. By comparing these vacation rentals, HomeToGo brings you the most economical offers and the highest rated properties in Cheshire.

Recommended Vacation Rentals in Cheshire

Find your perfect vacation rental in Cheshire: from $29 per night

House ∙ 6 guests ∙ 3 bedrooms
Berkshire, Lanesborough, Massachusetts, United States
from $218
VRBO
4.7
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Apartment ∙ 6 guests ∙ 2 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $179
VRBO
4.8
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House ∙ 5 guests ∙ 2 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $183
VRBO
4.8
View deal
House ∙ 6 guests ∙ 2 bedrooms
Adams, Berkshire County, Massachusetts, United States
from $198
VRBO
5.0
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Cabin ∙ 2 guests ∙ 1 bedroom
Cheshire, Berkshire County, Massachusetts, United States
from $132
Airbnb
5.0
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House ∙ 7 guests ∙ 3 bedrooms
Cheshire, Berkshire County, Massachusetts, United States
from $160
Airbnb
5.0
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House ∙ 2 guests ∙ 1 bedroom
Adams, Berkshire County, Massachusetts, United States
from $68
Airbnb
4.5
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Apartment ∙ 3 guests ∙ 2 bedrooms
Adams, Berkshire County, Massachusetts, United States
from $52
Airbnb
4.5
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Apartment ∙ 4 guests ∙ 2 bedrooms
Adams, Berkshire County, Massachusetts, United States
from $86
Airbnb
5.0
View deal
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Vacation Houses With Pools

Pool
Apartment ∙ 8 guests ∙ 1 bedroom
Hancock, Berkshire County, Massachusetts, United States
from $396
Airbnb
5.0
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Pool
Condo ∙ 8 guests ∙ 2 bedrooms
Hancock, Berkshire County, Massachusetts, United States
from $160
Airbnb
5.0
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Pool
Resort ∙ 8 guests ∙ 1 bedroom
Hancock, Berkshire County, Massachusetts, United States
from $110
Airbnb
5.0
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Vacation Rentals With Fireplaces

Fireplace
Bungalow ∙ 6 guests ∙ 2 bedrooms
Cheshire, Berkshire County, Massachusetts, United States
from $167
Airbnb
4.5
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Fireplace
House ∙ 10 guests ∙ 3 bedrooms
Cheshire, Berkshire County, Massachusetts, United States
from $294
Airbnb
4.5
View deal
Fireplace
House ∙ 9 guests ∙ 4 bedrooms
Hancock, Berkshire County, Massachusetts, United States
from $248
Airbnb
4.0
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests ∙ 1 bedroom
Cheshire, Berkshire County, Massachusetts, United States
from $44
VRBO
5.0
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Fishing
House ∙ 10 guests ∙ 3 bedrooms
Cheshire, Berkshire County, Massachusetts, United States
from $237
VRBO
4.7
View deal
Fishing
Private room ∙ 2 guests
Cheshire, Berkshire County, Massachusetts, United States
from $132
Booking.com
4.9
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Popular Rental Amenities in Cheshire

  • Kitchen (410)
  • Internet (391)
  • TV (357)
  • AC (298)
  • Washer (267)
  • Microwave (206)
  • Pool (203)
  • Grill (174)
  • Fireplace (172)
  • Parking (171)
  • Dishwasher (154)
  • No smoking (149)
Using our filters will help you find the ideal vacation rental in Cheshire. Most of the accommodations in Cheshire offer "TVs" or "internet," which makes it a wonderful vacation destination if you want to tune out with some TV time or you need internet access during your vacation. Not as many vacation rentals in Cheshire are available if you want a rental with a jacuzzi or if you travel with your pet as "Pets Allowed" and "Jacuzzis" are not very common amenities in Cheshire.

The Weather in Cheshire

34°
16°
34°
16°
43°
23°
57°
34°
70°
46°
77°
54°
81°
59°
79°
57°
73°
50°
61°
41°
48°
28°
39°
25°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above are the weather conditions for Cheshire. July is the warmest month in Cheshire with average maximum temperatures of 80°. On the other hand, you could have temperatures dropping under 15° in January. The rainiest month is July while the driest month is September.

Accommodations in Cheshire

In Cheshire, apartment rentals are the most prevalent accommodations being offered. In addition, these vacation accommodations have a median size of 890 ft² and an average price of $252 per night. Furthermore, these accommodations are ideal for medium-sized groups and families, as most can welcome 6 guests. House rentals are the other most common accommodation option in Cheshire. House rentals in Cheshire are 2,550 ft² on average, with prices averaging $332 per night.

Explore scenic Massachusetts with vacation rentals in Cheshire

Rural living is key in Cheshire, and most of the properties for vacation rentals are large, detached, and with plenty of room for the family to kick back and relax. Many properties stand in extensive grounds and enjoy views over the surrounding countryside.

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Family Activities

A vacation exploring the great outdoors

Kids will never be at a loose end in Cheshire. Hire a boat or kayak and get out on the lake or explore part of the Appalachian trail which cuts through the middle of town.

This part of Massachusetts is famous for its rolling landscape, and if you hike to the state's highest point at Mount Greylock, you can see up to 60 miles on a clear day.

Local Attractions

Discover Shaker culture in nearby Pittsfield

The living museum in Pittsfield gives a look into Shaker life. Explore the village's buildings, learn about construction methods, and meet the animals down on the farm. There are regular events during school vacations and visiting the museum is educational as well as entertaining.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Cheshire VRBO Vacation Rentals in Cheshire HomeAway Vacation Rentals in Cheshire TripAdvisor Vacation Rentals in Cheshire VacationRentals.com Vacation Rentals in Cheshire HouseTrip Vacation Rentals in Cheshire FlipKey Vacation Rentals in Cheshire 9flats.com Vacation Rentals in Cheshire VaycayHero Vacation Rentals in Cheshire PerfectPlaces.com Vacation Rentals in Cheshire Homestay.com Vacation Rentals in Cheshire Only-apartments Vacation Rentals in Cheshire Interhome Vacation Rentals in Cheshire Bedycasa Vacation Rentals in Cheshire Novasol Vacation Rentals in Cheshire HomeEscape Vacation Rentals in Cheshire

Vacation Destinations Near Cheshire