Cheshire Vacation Rentals - HomeToGo base64Hash Cheshire Vacation Rentals - HomeToGo

Cheshire Vacation Rentals

Find 15 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
1 km
2 km
5 km
Rating
4.5+
4+
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.

Show all 15 properties

Best Vacation Home Deals in Cheshire

Save up to 68%

House Cheshire
Oct 21 - Oct 28
-68%
$1,136
$360 per night
House ∙ 14 guests ∙ 5 bedrooms
House in Pittsfield with Grill
5.0
Outstanding (41 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cottage Cheshire
Sep 21 - Sep 28
-32%
$400
$271 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Rental Cottage in Hinsdale with Grill + Lake Views
4.7
Excellent (27 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
Sep 21 - Sep 28
-38%
$721
$449 per night
House ∙ 7 guests ∙ 4 bedrooms
House in Lanesborough with Grill + Lake Views
5.0
Outstanding (2 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Discover a vacation rental matching your needs among the 15 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.

Top-Rated Rentals and Accommodations in Cheshire

Book Vacation Rental Offers with the Highest User Rating

House Cheshire
Oct 21 - Oct 28
$201 per night
House ∙ 8 guests ∙ 2 bedrooms
Vacation Home in Hinsdale with Grill + Water Views
4.5
Excellent (67 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Bed and breakfast Cheshire
Nov 18 - Nov 25
$280 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
B&B in Cheshire with Yard
4.9
Outstanding (47 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
HomeToGo
View deal
View deal
House Cheshire
Nov 4 - Nov 11
$543 per night
House ∙ 14 guests ∙ 4 bedrooms
Nice Vacation Home in Hancock with Grill & Pool + Mountain Views
5.0
Outstanding (2 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Recommended Vacation Rentals in Cheshire

Find your perfect vacation rental in Cheshire: from $110 per night

Bed and breakfast Cheshire
Nov 11 - Nov 18
$253 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
Bed And Breakfast in Cheshire with Yard
Cheshire, Berkshire County, Massachusetts, United States
Details
Expedia
View deal
View deal
House Cheshire
Jan 20 - Jan 27
$221 per night
House ∙ 7 guests ∙ 3 bedrooms
House in Williamstown with Grill
5.0
Outstanding (94 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
Dec 23 - Dec 30
$200 per night
House ∙ 6 guests ∙ 5 bedrooms
Vacation Home in New Ashford with Yard & Grill
4.7
Excellent (64 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
Nov 4 - Nov 11
$550 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Pittsfield with Yard & Grill + Nice Views
5.0
Outstanding (92 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
Apr 13 - Apr 20
$339 per night
House ∙ 10 guests ∙ 5 bedrooms
Vacation Home in Dalton with Yard & Grill
4.9
Outstanding (45 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
Dec 1 - Dec 8
-26%
$648
$481 per night
House ∙ 6 guests ∙ 6 bedrooms
Vacation Home in Hinsdale with Yard, Patio & Grill
4.9
Outstanding (12 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cabin Cheshire
Dec 9 - Dec 16
$201 per night
Cabin ∙ 8 guests ∙ 3 bedrooms
Cabin in Hinsdale with Grill & Yard + Great View
5.0
Outstanding (17 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
Jun 22 - Jun 29
-16%
$310
$260 per night
House ∙ 4 guests ∙ 2 bedrooms
Lovely House in Pittsfield with Grill & Yard
4.9
Outstanding (96 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cabin Cheshire
Sep 21 - Sep 28
$300 per night
Cabin ∙ 5 guests ∙ 2 bedrooms
Cabin in Lanesborough with Grill + Beautiful Views
4.9
Outstanding (113 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
See all offers

Budget-friendly Vacation Rentals in Cheshire

Find Fantastic yet Inexpensive Offers

House Cheshire
Mar 30 - Apr 6
$200 per night
House ∙ 6 guests ∙ 4 bedrooms
Vacation Home in Hinsdale with Yard & Grill
5.0
Outstanding (53 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
Jun 15 - Jun 22
$150 per night
House ∙ 2 guests ∙ 1 bedroom
House in Lanesborough with Yard & Grill
4.8
Outstanding (236 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Cheshire
Mar 23 - Mar 30
-35%
$746
$486 per night
House ∙ 14 guests ∙ 5 bedrooms
Entire Vacation Home in Williamstown with Yard + Mountain Views
4.8
Outstanding (9 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Vacation Houses With Pools

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

House  Cheshire
Dec 9 - Dec 16
-30%
$876
$616 per night
House ∙ 8 guests ∙ 4 bedrooms
Nice Vacation Home in Williamstown with Pool, Grill & Yard
5.0
Outstanding (27 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pool
Details
Vrbo
View deal
View deal
House  Cheshire
Apr 6 - Apr 13
-60%
$1,500
$603 per night
House ∙ 16 guests ∙ 6 bedrooms
House in Pittsfield with Outdoor Pool
5.0
Outstanding (41 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pool
Details
Vrbo
View deal
View deal
House  Cheshire
Oct 21 - Oct 28
$290 per night
House ∙ 4 guests ∙ 1 bedroom
Vacation Home in Lanesborough with Yard & Pool + Mountain Views
4.8
Outstanding (8 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 in Cheshire!

House  Cheshire
Nov 18 - Nov 25
-18%
$261
$215 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Adams with Yard & Grill
5.0
Outstanding (108 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pet-friendly
Details
Vrbo
View deal
View deal
House  Cheshire
Mar 23 - Mar 30
-45%
$386
$213 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Adams with Edible Garden + Mountain Views
5.0
Outstanding (83 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Pet-friendly
Details
Vrbo
View deal
View deal
House  Cheshire
Dec 9 - Dec 16
-75%
$515
$131 per night
House ∙ 6 guests ∙ 3 bedrooms
Charming Vacation Home in Pittsfield with Grill & Yard + Beautiful Views
5.0
Outstanding (2 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 in Cheshire with their own private patios and balconies.

Condo  Cheshire
Nov 4 - Nov 11
-53%
$232
$110 per night
Condo ∙ 8 guests ∙ 2 bedrooms
Condo in Hancock with Jacuzzi, Grill & Yard
Cheshire, Berkshire County, Massachusetts, United States
Balcony
Details
HomeToGo
View deal
View deal
Apartment  Cheshire
Dec 2 - Dec 9
$151 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Rental Apartment in Hinsdale with Grill & Yard + Beautiful Views
5.0
Outstanding (30 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Balcony
Details
Vrbo
View deal
View deal
House  Cheshire
Nov 4 - Nov 11
-28%
$193
$139 per night
House ∙ 7 guests ∙ 3 bedrooms
Clean House in North Adams with Yard + Uninterrupted View
4.7
Excellent (6 ratings)
Cheshire, Berkshire County, Massachusetts, United States
Balcony
Details
Vrbo
View deal
View deal
See all offers

Popular Rental Amenities in Cheshire

  • Pet-friendly (1)
  • WiFi (15)
  • Fireplace (7)
  • Kitchen (1)
  • TV (14)
  • Balcony/patio (7)
  • Air conditioning (15)
  • Yard (15)
  • Washing machine (1)
  • Grill (1)
  • No smoking (9)
  • Fishing (8)

Using our filters will help you find the ideal vacation rental in Cheshire. Most of the accommodations in Cheshire offer "Pets allowed" or "Internet," which makes it a wonderful vacation destination if you travel with your pet or you can't imagine a vacation without internet. Not as many vacation rentals in Cheshire are available if you want to go fishing or if you want to be able to quickly warm up your meals as "Microwave" and "Fishing" are not very common amenities in Cheshire.

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

Wed, 27 Sep
66°
50°

10%

9 h

2 mi/h

Thu, 28 Sep
60°
48°

0%

8 h

4 mi/h

Fri, 29 Sep
50°
46°

15%

0 h

5 mi/h

Sat, 30 Sep
62°
50°

15%

2 h

4 mi/h

Sun, 1 Oct
60°
46°

10%

9 h

6 mi/h

Mon, 2 Oct
66°
46°

0%

10 h

4 mi/h

Tue, 3 Oct
71°
57°

10%

11 h

3 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 68%
🌙 Nightly prices starting at $110
⭐ Popular amenities Pets allowed, Internet and Fireplace
🐾 Pet friendly homes 1 homes

Frequently Asked Questions

What is the average price per night for a vacation rental in Cheshire?

The average accommodation in Cheshire is priced at $110 per night. If you are looking for a bed and breakfast rental, the nightly price is $291 on average. A house rental Cheshire will cost on average $441 per night.

How many vacation homes are available for booking in Cheshire?

There are currently 15 vacation homes to choose from for your trip.

What amenities are most popular for vacation homes in Cheshire?

Travelers look for Pets allowed, Internet, and Fireplace when booking a vacation rental in Cheshire.

Are pets allowed in vacation rentals in Cheshire?

In case if you are traveling with a dog in Cheshire - 7% of vacation homes are pet-friendly.

What's the best month to travel to Cheshire?

If you are choosing a vacation home in Cheshire, consider that rainy season is usually in December or January, with September often being the driest.

Vacation Destinations Near Cheshire

Show more

Top Vacation Ideas

Explore More Vacation Ideas

Show more
image-tag