A lake surrounded by autumn-colored trees and hills.

Find Cheap Hotels in Cheshire, MA from CA $138

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Cheshire Cheap Hotels

Tonight
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Cheshire cheap hotels

Exterior
TV
Garden
View from property

1. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
CA $318
CA $336 total
includes taxes & fees
Sep 16 - Sep 17
Harbour House Inn
Hypo-allergenic bedding available, desk, laptop workspace
Daily to-go breakfast for a fee
Hypo-allergenic bedding available, desk, laptop workspace
Banquet hall

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
CA $163
CA $182 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
Lobby sitting area
Exterior
Property amenity

3. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Prasanna
CA $124
CA $138 total
includes taxes & fees
Sep 13 - Sep 14
Best Western Plus Berkshire Hills Inn & Suites
Lobby
Lobby sitting area
Indoor pool, outdoor pool, pool umbrellas
Front of property - evening/night

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Sarah
CA $131
CA $162 total
includes taxes & fees
Sep 15 - Sep 16
Vacation Village in the Berkshires
Courtyard
Cabin, 3 Bedrooms, Mountainside | Living area
Breakfast meal
Seasonal outdoor pool

5. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $157
CA $172 total
includes taxes & fees
Sep 13 - Sep 14
The Springs Motel
55-inch LCD TV with digital channels, printers
Front of property
Reception
Romantic Room, 1 King Bed (Room 4)

6. The Revival House

The Revival House
Adams
United States
James
CA $228
CA $255 total
includes taxes & fees
Sep 13 - Sep 14
The Revival House
Hypo-allergenic bedding available, desk, laptop workspace
Exterior
Coffee service
Front of property

7. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Basil
CA $197
CA $220 total
includes taxes & fees
Sep 30 - Oct 1
Hotel Downstreet, an Ascend Collection Hotel
Mountain view
Dining
Desk, iron/ironing board, cribs (free), rollaway beds (free)
Front of property - evening/night

8. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
Williamstown
United States
Donna
CA $150
CA $167 total
includes taxes & fees
Oct 7 - Oct 8
Howard Johnson by Wyndham Williamstown
Property grounds
Desk, iron/ironing board (on request), cribs (surcharge), WiFi (free)
Property grounds
Exterior

9. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
Chris
CA $143
CA $159 total
includes taxes & fees
Sep 15 - Sep 16
Willows Motel Williamstown
Property entrance
Library Suite, 1 King Bed
Lunch and dinner served
Lobby

10. Hotel On North

Hotel On North
Pittsfield
United States
Drew
CA $185
CA $207 total
includes taxes & fees
Sep 15 - Sep 16
Hotel On North
View all properties

Top Cheshire Hotel Reviews

FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"Room was clean and comfortable."
Mark 2-night trip
Posted 10 hours ago
FairBridge Inn Express
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Always a great stay at. Vacation Villages"
Susan 1-night trip
Posted 18 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
Joanne 2-night trip
Posted 18 hours ago
The Yankee Inn
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Awesome staff plus pet-friendly."
Gina 1-night trip
Posted 1 day ago
Willows Motel Williamstown
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Generous front desk (forgot toothbrush & comb, they gave us both free of charge). Great complimentary breakfast & tea/coffee machine. Great WiFi. Beautiful view & kayaking was so fun. We had a wonderful stay!"
Kimberly 2-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"Friendly staff. Good location."
Joe 1-night trip
Posted 1 day ago
Best Western Plus Berkshire Hills Inn & Suites
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."
Mary 1-night trip
Posted 2 days ago
Quality Inn Lee - Lenox South
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Nice and conveniently located"
Lina 3-night trip
Posted 3 days ago
Hotel Downstreet, an Ascend Collection Hotel

Frequently asked questions

What is Cheshire like for travelers on a budget?
Discover cheap places to stay in Cheshire on Expedia.com and plan a vacation that stays within your budget. You can browse a wide offering of hotels and other accommodations with Member Prices to find the best deal for you. With our site's handy page filters, you can search by your price range, or by amenities that customers often look for like free breakfast and free parking. If you're hoping for reasonable options around local sights, such as Mount Greylock State Reservation or Cheshire Reservoir, try out the location filters to narrow down your search. As you browse, click the heart button to keep track of your favorites so that you can come back to them when you're ready to book. Interested in a car or a flight too? Take a look at the vacation packages available under Bundle and Save and discover huge discounts by reserving transportation at the same time.
When is the best time for a budget trip to Cheshire?
Weather will likely play an important role when you plan your trip to Cheshire, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to see and do in Cheshire?
You won't have to spend a fortune to find places to visit in Cheshire. You can budget for the local attractions that interest you most, and then make time for sights and activities that are easy on the wallet. If you're eager to get outdoors, you can enjoy the natural setting at Mount Greylock State Reservation, Cheshire Reservoir, or Mount Greylock State Reservation Visitor Center.
How can I get to Cheshire and get around on a budget?
Scoping out the transportation options in Cheshire can help keep you on budget. The closest airport is Pittsfield, MA (PSF-Pittsfield Municipal), situated 11.5 mi (18.5 km) away. However, if that doesn't suit your budget, you can arrange flights in and out of Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. Cheshire may not have many public transit options so a rental car could be a reasonable alternative to explore more of the area.

Explore a world of travel with Expedia