Cheshire Vacation Rentals

Compare 9 available properties from 12 providers
Cheshire
Check-in
2 guests

Discover a vacation rental matching your needs among the 9 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 $36 per night

Fishing
House ∙ 4 guests ∙ 1 bedroom
Cheshire, Berkshire County, Massachusetts, United States
from $44
Vrbo
4.7
View deal
Fishing
House ∙ 10 guests ∙ 3 bedrooms
Cheshire, Berkshire County, Massachusetts, United States
from $237
Vrbo
4.7
View deal
Fishing
Bed & Breakfast ∙ 2 guests
Cheshire, Berkshire County, Massachusetts, United States
from $189
Booking.com
4.9
View deal
See all offers

Popular Rental Amenities in Cheshire

  • Internet (14)
  • AC (11)
  • Kitchen (10)
  • TV (8)
  • Washer (8)
  • Yard (6)
  • Parking (5)
  • No smoking (5)
  • Pet allowed (4)
  • Grill (4)
  • Microwave (4)
  • Fireplace (3)
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 December while the driest month is September.

Accommodations in Cheshire

In Cheshire, house rentals are the most prevalent accommodations being offered. In addition, these vacation accommodations have a median size of 2,490 ft² and an average price of $263 per night. Furthermore, these accommodations are ideal for large groups, as most can welcome 7 guests. Private rooms are the other most common accommodation option in Cheshire. Private rooms in Cheshire are 1,120 ft² on average, with prices averaging $78 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.

Show all 9 properties
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 600 providers, including:

Booking.com Vacation Rentals in Cheshire Vrbo Vacation Rentals in Cheshire HomeAway Vacation Rentals in Cheshire Airbnb 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

image-tag