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Cheshire Vacation Rentals

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Cheshire
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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+

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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Save up to 27%

Best Vacation Home Deals in Cheshire

House Cheshire
Oct 21 - Oct 28
-27%
$638
$464 per night
House ∙ 8 guests ∙ 4 bedrooms
Charming House in Cheshire with 2-Car Garage + Mountain View
5.0
"Excellent" (1 rating)
Cheshire, Berkshire County, Massachusetts, United States
Details
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Condo Cheshire
May 7 - May 14
-17%
$235
$195 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Nice Condo in Hancock with Ample Parking
4.7
"Outstanding" (11 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
Apr 8 - Apr 15
-19%
$216
$176 per night
House ∙ 6 guests ∙ 4 bedrooms
Vacation Home in Hinsdale with Yard & Grill
5.0
"Excellent" (53 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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Discover a vacation rental matching your needs among the 18 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.

Book Vacation Rental Offers with the Highest User Rating

Top-Rated Rentals and Accommodations in Cheshire

House Cheshire
Mar 16 - Mar 23
-46%
$282
$153 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Lanesborough with Yard
4.7
"Outstanding" (67 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
Sep 2 - Sep 9
$196 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Cummington with Yard & Grill + River Views
4.7
"Outstanding" (34 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
May 13 - May 20
-32%
$650
$444 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
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Recommended Vacation Rentals in Cheshire

Find your perfect vacation rental in Cheshire: from $153 per night

House Cheshire
Oct 21 - Oct 28
$469 per night
House ∙ 8 guests ∙ 4 bedrooms
Charming House in Cheshire with 2-Car Garage + Mountain View
5.0
"Excellent" (1 rating)
Cheshire, Berkshire County, Massachusetts, United States
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Bed & Breakfast Cheshire
Jun 17 - Jun 24
$307 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
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Condo Cheshire
Apr 22 - Apr 29
-17%
$234
$195 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Nice Condo in Hancock with Ample Parking
4.7
"Outstanding" (11 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
Apr 8 - Apr 15
-19%
$215
$176 per night
House ∙ 6 guests ∙ 4 bedrooms
Vacation Home in Hinsdale with Yard & Grill
5.0
"Excellent" (54 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
Sep 30 - Oct 7
$188 per night
House ∙ 6 guests ∙ 3 bedrooms
Whole Vacation Home in Lanesborough with Electric Fireplace
5.0
"Excellent" (92 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
Sep 16 - Sep 23
-46%
$469
$252 per night
House ∙ 10 guests ∙ 3 bedrooms
Wonderful Vacation Home in Pittsfield with Grill
4.7
"Outstanding" (69 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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Cabin Cheshire
Sep 16 - Sep 23
$280 per night
Cabin ∙ 5 guests ∙ 3 bedrooms
Cabin in Lanesborough with Yard & Grill + Beautiful Views
5.0
"Excellent" (108 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
Jan 20 - Jan 27
-52%
$352
$170 per night
House ∙ 6 guests ∙ 3 bedrooms
Wonderful House in Lanesborough with Electric Fireplace + Mountain Views
5.0
"Excellent" (1 rating)
Cheshire, Berkshire County, Massachusetts, United States
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Cottage Cheshire
Apr 22 - Apr 29
-28%
$258
$185 per night
Cottage ∙ 5 guests ∙ 3 bedrooms
Cottage in Pittsfield with Free Parking
5.0
"Excellent" (9 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Cheshire

House Cheshire
Sep 9 - Sep 16
$201 per night
House ∙ 7 guests ∙ 4 bedrooms
Vacation Home in North Adams with Grill & Yard
5.0
"Excellent" (10 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
Dec 9 - Dec 16
$338 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Dalton with Yard & Grill
4.9
"Excellent" (44 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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House Cheshire
Sep 16 - Sep 23
$200 per night
House ∙ 2 guests ∙ 1 bedroom
House in Lanesborough with Yard & Grill
4.9
"Excellent" (229 ratings)
Cheshire, Berkshire County, Massachusetts, United States
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Vacation Houses With Pools

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

Condo Pool Cheshire
Feb 3 - Feb 10
$365 per night
Condo ∙ 8 guests ∙ 2 bedrooms
Condo in Hancock with Outdoor Pool
5.0
"Excellent" (31 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pool
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Condo Pool Cheshire
Apr 1 - Apr 8
-25%
$385
$289 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Condo in Hancock with Grill, Pool & Yard
5.0
"Excellent" (87 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pool
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House Pool Cheshire
May 5 - May 12
$400 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Pittsfield with Grill & Pool
5.0
"Excellent" (1 rating)
Cheshire, Berkshire County, Massachusetts, United States
Pool
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Dog-Friendly Vacation Rentals

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

House Pet-friendly Cheshire
Sep 9 - Sep 16
$201 per night
House ∙ 7 guests ∙ 4 bedrooms
Vacation Home in North Adams with Grill & Yard
5.0
"Excellent" (10 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pet-friendly
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House Pet-friendly Cheshire
Mar 23 - Mar 30
-46%
$282
$153 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Lanesborough with Yard
4.7
"Outstanding" (67 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pet-friendly
Details
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House Pet-friendly Cheshire
Dec 9 - Dec 16
$338 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Dalton with Yard & Grill
4.9
"Excellent" (44 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pet-friendly
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Best vacation rentals with a balcony

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

House Balcony Cheshire
May 6 - May 13
-32%
$650
$444 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
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House Balcony Cheshire
Sep 2 - Sep 9
$196 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Cummington with Yard & Grill + River Views
4.7
"Outstanding" (34 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Balcony
Details
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House Balcony Cheshire
May 5 - May 12
-21%
$1,901
$1,500 per night
House ∙ 9 guests ∙ 5 bedrooms
House in Pittsfield with Yard, Grill & Sauna
5.0
"Excellent" (34 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Balcony
Details
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Popular Rental Amenities in Cheshire

  • Yard (18)
  • Internet (18)
  • Air conditioning (17)
  • TV (15)
  • No smoking (12)
  • No pets (8)
  • Fishing (7)
  • Fireplace (5)
  • Pets allowed (4)
  • Kitchen (4)
  • Washer (4)
  • Microwave (4)

The Weather in Cheshire

max.
Min.
34°
16°
17 days 17
max.
Min.
34°
16°
17 days 17
max.
Min.
43°
23°
16 days 16
max.
Min.
57°
34°
14 days 14
max.
Min.
70°
46°
14 days 14
max.
Min.
77°
54°
14 days 14
max.
Min.
81°
59°
13 days 13
max.
Min.
79°
57°
11 days 11
max.
Min.
73°
50°
10 days 10
max.
Min.
61°
41°
14 days 14
max.
Min.
48°
28°
13 days 13
max.
Min.
39°
25°
20 days 20
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 81°. On the other hand, you could have temperatures dropping under 16° in January. The rainiest month is December while the driest month is September.

7-Day Weather Forecast in Cheshire

Sat, 1 Apr
59°
46°

15%

2 h

13 mi/h

Sun, 2 Apr
35°
19°

15%

9 h

10 mi/h

Mon, 3 Apr
53°
33°

15%

3 h

12 mi/h

Tue, 4 Apr
50°
39°

5%

2 h

4 mi/h

Wed, 5 Apr
50°
42°

15%

0 h

5 mi/h

Thu, 6 Apr
59°
41°

15%

0 h

12 mi/h

Fri, 7 Apr
46°
32°

0%

5 h

4 mi/h

Accommodations for your vacation in Cheshire

In Cheshire, bed & breakfast rentals are the most prevalent accommodations being offered. In addition, these vacation accommodations have a median size of 20 ft² and an average price of $248 per night. Furthermore, these accommodations are ideal for couples and small groups, as most can welcome 2 guests. Farmhouse rentals are the other most common accommodation option in Cheshire. Farmhouse rentals in Cheshire are 1,120 ft² on average, with prices averaging $398 per night.
What are the best activities for families in Cheshire?

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.

Where are the unique attractions in Cheshire?

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.

Information about vacation rentals in Cheshire

💳 Possible discounts up to 34%
🌙 Nightly prices starting at $153
⭐ Popular amenities Yard, Internet and Air conditioning
🐾 Pet friendly accommodations 4 properties

Frequently Asked Questions

What is the typical nightly price for a vacation rental in Cheshire?

The nightly price of accommodations in Cheshire starts at $153. If you would like to stay in a bed & breakfast, the average price is $321 per night. A house rental Cheshire will cost $610 per night on average.

How many vacation rentals are available to book in Cheshire?

There are 18 vacation rentals from 5 different providers in Cheshire.

What are the most popular amenities for vacation homes in Cheshire?

Most travelers search for Yard, Internet, and Air conditioning when booking a vacation rental in Cheshire.

Are pets allowed in vacation rentals in Cheshire?

If you are traveling with a dog in Cheshire - 19% of vacation homes allow pets.

When is it better to travel to Cheshire?

Cheshire has its warmest time of year in July and August, with average prices of $153 per night.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Cheshire TripAdvisor Vacation Rentals in Cheshire Vrbo Vacation Rentals in Cheshire VacationRentals.com Vacation Rentals in Cheshire HouseTrip Vacation Rentals in Cheshire FlipKey Vacation Rentals in Cheshire Homestay.com Vacation Rentals in Cheshire Only-apartments Vacation Rentals in Cheshire Interhome Vacation Rentals in Cheshire Novasol Vacation Rentals in Cheshire HomeEscape Vacation Rentals in Cheshire

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