Cheshire Vacation Rentals

Compare 196 available properties from 18 providers
Cheshire

Discover a vacation rental matching your needs among the 191 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

Rent a vacation accommodation in Cheshire: from $51 per night

House ∙ 5 guests ∙ 2 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $183
VRBO
4.8
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House ∙ 10 guests ∙ 5 bedrooms
Dalton, Berkshire County, Massachusetts, United States
from $322
VRBO
5.0
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House ∙ 14 guests ∙ 7 bedrooms
Adams, Berkshire County, Massachusetts, United States
from $412
VRBO
5.0
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Apartment ∙ 4 guests ∙ 1 bedroom
Lanesborough, Berkshire County, Massachusetts, United States
from $49
VRBO
4.8
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Apartment ∙ 6 guests ∙ 2 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $139
VRBO
4.3
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House ∙ 5 guests ∙ 2 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $277
VRBO
4.8
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House ∙ 12 guests ∙ 4 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $268
VRBO
4.8
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Apartment ∙ 4 guests ∙ 2 bedrooms
Hancock, Berkshire County, Massachusetts, United States
from $201
VRBO
5.0
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Private room ∙ 2 guests
Cheshire, Berkshire County, Massachusetts, United States
from $241
Booking.com
4.9
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Vacation Rentals With Fireplaces

Fireplace
Apartment ∙ 6 guests ∙ 2 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $229
VRBO
4.8
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Fireplace
Apartment ∙ 10 guests ∙ 4 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $296
VRBO
4.5
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Fireplace
House ∙ 9 guests ∙ 3 bedrooms
Hinsdale, Berkshire County, Massachusetts, United States
from $360
VRBO
4.8
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Vacation Houses With Pools

Pool
Apartment ∙ 8 guests ∙ 2 bedrooms
Hancock, Berkshire County, Massachusetts, United States
from $142
VRBO
4.8
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Pool
Apartment ∙ 8 guests ∙ 2 bedrooms
Hancock, Berkshire County, Massachusetts, United States
from $157
VRBO
5.0
View deal
Pool
Private room ∙ 2 guests
Adams, Berkshire County, Massachusetts, United States
from $273
Booking.com
4.3
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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 ∙ 6 guests ∙ 3 bedrooms
Berkshire, Lanesborough, Massachusetts, United States
from $263
VRBO
4.7
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Fishing
House ∙ 6 guests ∙ 2 bedrooms
Adams, Berkshire County, Massachusetts, United States
from $195
VRBO
5.0
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Popular Rental Amenities in Cheshire

  • Kitchen (178)
  • Internet (177)
  • TV (174)
  • Parking (167)
  • No smoking (167)
  • AC (155)
  • No pets (138)
  • Grill (137)
  • Microwave (127)
  • Pool (117)
  • Fireplace (113)
  • Dishwasher (107)
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 860 ft² and an average price of $255 per night. Furthermore, these accommodations are ideal for large groups, as most can welcome 7 guests. House rentals are the other most common accommodation option in Cheshire. House rentals in Cheshire are 2,570 ft² on average, with prices averaging $460 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