Cheshire Vacation Rentals - HomeToGo base64Hash Cheshire Vacation Rentals - HomeToGo

Cheshire Vacation Rentals

Find 18 available offers from 5 partners
Cheshire
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+
Save up to 42%

Best Vacation Home Deals Cheshire

House Cheshire
Mar. 11 - Mar. 18
-42%
$585
$340 per night
House ∙ 6 guests ∙ 3 bedrooms
Family Friendly Nice Vacation Home in Hancock with Wood-Burning Fireplace
4.9
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Evolve
View deal
View deal

Find the perfect rental for as little as $241 per night by exploring the 18 properties being offered in Cheshire. Using HomeToGo's search feature you can immediately compare the offers of each available rental to find the best deal and save up to 42%.

Book Vacation Rentals with the Highest User Rating

Top-Rated Offers and Accommodations Cheshire

House Cheshire
$353 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Cheshire with Grill & Yard + Mountain Views
4.7
"Outstanding" (83 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
$423 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Cheshire with Yard & Grill + Mountain Views
4.7
"Outstanding" (56 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Expedia
View deal
View deal
House Cheshire
$742 per night
House ∙ 8 guests ∙ 4 bedrooms
Entire House in Cheshire with 2-Car Garage
5.0
"Excellent" (1 rating)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Recommended Vacation Rentals Cheshire

Find your perfect vacation rental Cheshire: from $241 per night

House Cheshire
$760 per night
House ∙ 8 guests ∙ 4 bedrooms
Entire Vacation Home in Cheshire with 2-Car Garage
5.0
"Excellent" (1 rating)
Cheshire, Berkshire County, Massachusetts, United States
Details
Expedia
View deal
View deal
Bed & Breakfast Cheshire
$446 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Bed And Breakfast in Cheshire with Yard
4.9
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
HomeToGo
View deal
View deal
Bed & Breakfast Cheshire
$380 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Bed & Breakfast in Cheshire with Yard
4.9
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
HomeToGo
View deal
View deal
Bed & Breakfast Cheshire
$429 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Bed & Breakfast in Cheshire with Yard
4.9
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
HomeToGo
View deal
View deal
Bed & Breakfast Cheshire
$429 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Charming Bed & Breakfast in Cheshire with Yard
4.9
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
HomeToGo
View deal
View deal
See all offers
Find Fantastic yet Inexpensive Rentals

Budget-friendly Rentals Cheshire

House Cheshire
Aug. 5 - Aug. 12
$440 per night
House ∙ 8 guests ∙ 2 bedrooms
Nice Vacation Home in Hancock with Pool, Sauna & Yard
5.0
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Bed & Breakfast Cheshire
$402 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Beautiful Bed And Breakfast in Cheshire with Yard + Garden View
4.9
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
HomeToGo
View deal
View deal
Bed & Breakfast Cheshire
$445 per night
Bed & Breakfast ∙ 3 guests ∙ 1 bedroom
B&B in Cheshire with Yard
4.9
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
HomeToGo
View deal
View deal

Vacation Houses with Pools

Make a splash on your next vacation! Over 0% of Cheshire vacation rentals have a swimming pool.

House Pool Cheshire
$241 per night
House ∙ 8 guests ∙ 2 bedrooms
Nice Vacation Home in Hancock with Pool, Sauna & Yard
5.0
"Excellent" (20 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pool
Details
Vrbo
View deal
View deal
Condo Pool Cheshire
$516 per night
Condo ∙ 8 guests ∙ 2 bedrooms
Nice Condo in Hancock with Sauna, Pool & Grill
4.9
"Excellent" (70 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pool
Details
Vrbo
View deal
View deal
Condo Pool Cheshire
$351 per night
Condo ∙ 10 guests ∙ 3 bedrooms
Condo in Hancock with Electric Fireplace + Panoramic Views
5.0
"Excellent" (45 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pool
Details
Vrbo
View deal
View deal
See all offers

Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals Cheshire!

House Pet-friendly Cheshire
$389 per night
House ∙ 4 guests ∙ 8 bedrooms
Family Friendly Vacation Home in Pittsfield with Electric Fireplace + Beautiful Views
4.9
"Excellent" (120 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pet-friendly
Details
Vrbo
View deal
View deal
House Pet-friendly Cheshire
$367 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Plainfield with Vegetable Garden
4.8
"Excellent" (61 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pet-friendly
Details
Vrbo
View deal
View deal
House Pet-friendly Cheshire
$360 per night
House ∙ 4 guests ∙ 1 bedroom
Lovely House in Pittsfield with Grill & Yard
4.8
"Excellent" (85 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pet-friendly
Details
Vrbo
View deal
View deal
See all offers

Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes Cheshire with their own private patios and balconies.

House Balcony Cheshire
$697 per night
House ∙ 6 guests ∙ 6 bedrooms
Vacation Home in Hinsdale with Yard & Grill
4.9
"Excellent" (12 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Balcony
Details
Vrbo
View deal
View deal
Condo Balcony Cheshire
$309 per night
Condo ∙ 9 guests ∙ 2 bedrooms
Condo in Hancock with Electric Fireplace + Panoramic Views
4.9
"Excellent" (8 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Balcony
Details
Vrbo
View deal
View deal
Condo Balcony Cheshire
$253 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Hancock with Sauna, Pool & Yard
4.4
"Very good" (12 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Balcony
Details
Vrbo
View deal
View deal
See all offers

Popular Rental Amenities Cheshire

  • Internet (18)
  • Yard (18)
  • Air conditioning (17)
  • TV (15)
  • No smoking (12)
  • Fishing (9)
  • No pets (8)
  • Fireplace (5)
  • Pet allowed (4)
  • Kitchen (4)
  • Washer (4)
  • Microwave (4)

Use filters to search and find an accommodation matching your needs among the 18 rentals in Cheshire. Cheshire is the right place to book a rental if you need internet access during your vacation or you want a rental with a yard, as the most frequently offered amenities are "Internet" and "Yard." Plan your vacation in advance if you love to grill out or you travel with your pet. There are just 2 listed properties with "Barbecue" and 4 rentals providing "Pets allowed."

The Weather Cheshire

max.
Min.

-9°
17 days 17
max.
Min.

-9°
17 days 17
max.
Min.

-5°
16 days 16
max.
Min.
14°
14 days 14
max.
Min.
21°
14 days 14
max.
Min.
25°
12°
14 days 14
max.
Min.
27°
15°
13 days 13
max.
Min.
26°
14°
11 days 11
max.
Min.
23°
10°
10 days 10
max.
Min.
16°
14 days 14
max.
Min.

-2°
13 days 13
max.
Min.

-4°
20 days 20
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. During July, maximum temperatures go up to more than 27° Conversely, January is the coolest month Cheshire, with temperatures going under -9° The wettest month is December with 20 rainy days on average. On the contrary, there is an average of only 10 rainy days in September, which is the driest month.

7-Day Weather Forecast Cheshire

Wed., 8 Feb.
-3°

15%

3 h

16 km/h

Thu., 9 Feb.
-2°

15%

0 h

9 km/h

Fri., 10 Feb.

15%

0 h

22 km/h

Sat., 11 Feb.
-1°
-4°

15%

5 h

10 km/h

Sun., 12 Feb.
-5°

0%

6 h

3 km/h

Mon., 13 Feb.
-4°

0%

8 h

4 km/h

Tue., 14 Feb.
-1°

15%

3 h

11 km/h

Frequently Asked Questions

What is the typical price of a vacation home Cheshire?

The starting price for Bed & Breakfast rentals or House rentals Cheshire is $241 per night.

What is the typical availability of Bed & Breakfast rentals Cheshire?

We found 18 vacation homes Cheshire available for your next trip.

What are the most popular vacation home amenities Cheshire?

Many travellers are searching for Internet, Yard, and TV when booking a vacation home Cheshire.

How many Bed & Breakfast rentals and House rentals can I find Cheshire?

Cheshire has 18 Bed & Breakfast rentals and House rentals available to book.

Are there pet-friendly vacation rentals Cheshire?

Finding a vacation rental Cheshire that allows dogs is definitely possible, with 4 pet-friendly homes on offfer.

What's the best month to visit Cheshire?

When booking accommodation Cheshire, remember that the rainiest months are usually December and January, with September often being the sunniest.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals Cheshire TripAdvisor Vacation Rentals Cheshire Vrbo Vacation Rentals Cheshire Novasol Vacation Rentals Cheshire Inter Chalet Vacation Rentals Cheshire Interhome Vacation Rentals Cheshire HouseTrip Vacation Rentals Cheshire Belvilla Vacation Rentals Cheshire Homestay.com Vacation Rentals Cheshire Ski Planet Vacation Rentals Cheshire Only-apartments Vacation Rentals Cheshire James Villa Holidays Vacation Rentals Cheshire

Vacation Destinations Near Cheshire

Top Vacation Ideas

Explore More Vacation Ideas

image-tag