Cheshire Vacation Rentals

Compare 155 available properties from 14 providers
Cheshire
Save up to 44%

Best vacation home deals in Cheshire

$274
from $153
-44%
1590 ft² House
6 2
Lanesborough, Berkshire County, Massachusetts, United States
Found on
HomeAway
$458
from $356
-22%
1740 ft² Apartment
10 4
Lanesborough, Berkshire County, Massachusetts, United States
Found on
HomeAway
$265
from $161
-39%
2200 ft² House
10 3
Lanesborough, Berkshire County, Massachusetts, United States
Found on
HomeAway

Discover a vacation rental matching your needs among the 155 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 $61 per night

$274
from $153
-44%
1590 ft² House
6 2
Lanesborough, Berkshire County, Massachusetts, United States
4.9
"Excellent" 171 reviews
Found on HomeAway
$322
from $265
-18%
House
10 5
Dalton, Berkshire County, Massachusetts, United States
5.0
"Excellent" 17 reviews
Found on HomeAway
from $186
1190 ft² House
7 3
Lanesborough, Berkshire County, Massachusetts, United States
5.0
"Excellent" 3 reviews
Found on HomeAway
$265
from $161
-39%
2200 ft² House
10 3
Lanesborough, Berkshire County, Massachusetts, United States
4.9
"Excellent" 41 reviews
Found on HomeAway
from $409
House
14 7
Adams, Berkshire County, Massachusetts, United States
4.9
"Excellent" 33 reviews
Found on HomeAway
from $108
800 ft² Apartment
4 1
Lanesborough, Berkshire County, Massachusetts, United States
4.8
"Excellent" 55 reviews
Found on HomeAway
$181
from $138
-24%
590 ft² Apartment
6 2
Lanesborough, Berkshire County, Massachusetts, United States
4.3
"Outstanding" 7 reviews
Found on HomeAway
from $250
House
5 2
Pittsfield, Berkshire County, Massachusetts, United States
4.7
"Excellent" 7 reviews
Found on HomeAway
See all offers

  Vacation homes with fishing spots nearby

$235
from $179
-24%
1250 ft² Apartment
6 2
Lanesborough, Berkshire County, Massachusetts, United States
4.8
"Excellent" 71 reviews
Found on HomeAway
$372
from $237
-36%
House
10 3
Cheshire, Berkshire County, Massachusetts, United States
4.7
"Excellent" 27 reviews
Found on HomeAway
$241
from $188
-22%
1400 ft² House
6 3
Berkshire, Lanesborough, Massachusetts, United States
4.7
"Excellent" 26 reviews
Found on HomeAway
$458
from $356
-22%
1740 ft² Apartment
10 4
Lanesborough, Berkshire County, Massachusetts, United States
4.5
"Outstanding" 7 reviews
Found on HomeAway
See all offers

  Vacation rentals with a fireplace

$158
from $116
-26%
House
4 2
Adams, Berkshire County, Massachusetts, United States
4.7
"Excellent" 14 reviews
Found on HomeAway
from $407
3000 ft² House
9 3
Hinsdale, Berkshire County, Massachusetts, United States
4.8
"Excellent" 9 reviews
Found on HomeAway
from $347
Topia Inn
2 1
Adams, Berkshire County, Massachusetts, United States
4.7
"Excellent" 7 reviews
Found on Booking.com
$559
from $473
-15%
2500 ft² House
12 4
Lanesborough, Berkshire County, Massachusetts, United States
4.9
"Excellent" 18 reviews
Found on HomeAway
See all offers

Popular rental amenities in Cheshire

  • Kitchen (121)
  • TV (121)
  • Internet (120)
  • No smoking (110)
  • AC (97)
  • Microwave (97)
  • Parking (95)
  • Washer (88)
  • Grill (83)
  • Dishwasher (83)
  • No pets (74)
  • Fireplace (63)
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 love sweating the stress away in saunas or if you travel with your pet as "Pets Allowed" and "saunas" 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

Check out the climate diagram for Cheshire. On average, the warmest month is July. However, temperatures can go lower than 15° in Cheshire in January. September is the driest month.

In Cheshire, house rentals are the most prevalent accommodations being offered. In addition, these vacation accommodations have a median size of 2,470 ft² and an average price of $422 per night. Furthermore, these accommodations are ideal for large groups, as most can welcome 8 guests. Apartment rentals are the other most common accommodation option in Cheshire. Apartment rentals in Cheshire are 1,150 ft² on average, with prices averaging $252 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 155 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 250 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 Wimdu 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