A lake surrounded by autumn-colored trees and hills.

Find Cheap Hotels in Cheshire, MA from CA $96

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Check availability on Cheshire Cheap Hotels

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Cheshire cheap hotels

Exterior
Exterior
TV
View from property

1. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
CA $320
CA $339 total
includes taxes & fees
Sep 16 - Sep 17
Harbour House Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
Property amenity
Lobby sitting area
In-room safe, desk, laptop workspace, blackout drapes

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Joe
CA $152
CA $170 total
includes taxes & fees
Sep 15 - Sep 16
Best Western Plus Berkshire Hills Inn & Suites
Courtyard
Honeymoon Suite, 1 King Bed, Patio
Breakfast meal
Cabin, 3 Bedrooms, Mountainside | Living area

3. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $154
CA $169 total
includes taxes & fees
Sep 13 - Sep 14
The Springs Motel
Lobby
Exterior
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 $132
CA $162 total
includes taxes & fees
Sep 15 - Sep 16
Vacation Village in the Berkshires
Desk, iron/ironing board, WiFi (free), bed sheets
Fitness facility
Business centre
Standard Room, 1 King Bed, Non Smoking

5. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
Horace
CA $86
CA $96 total
includes taxes & fees
Sep 24 - Sep 25
FairBridge Inn Express
55-inch LCD TV with digital channels, printers
Front of property
Romantic Room, 1 King Bed (Room 4)
Game room

6. The Revival House

The Revival House
Adams
United States
James
CA $229
CA $256 total
includes taxes & fees
Sep 27 - Sep 28
The Revival House
Superior Room, 1 King Bed, Jetted Tub | Jetted tub
View from room
42-inch flat-screen TV with cable channels, TV
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

7. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
CA $145
CA $162 total
includes taxes & fees
Sep 22 - Sep 23
The Yankee Inn
Gazebo
Point of interest
Front of property
Standard Room, 1 Queen Bed, Non Smoking

8. Cozy Corner Motel

Cozy Corner Motel
Williamstown
United States
Janis
CA $122
CA $143 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Corner Motel
Hypo-allergenic bedding available, desk, laptop workspace
Hypo-allergenic bedding available, desk, laptop workspace
Hypo-allergenic bedding available, desk, laptop workspace
Daily to-go breakfast for a fee

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
CA $160
CA $178 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Standard Room, 1 King Bed, Non Smoking
Exterior
Standard Room, 1 King Bed, Non Smoking
Minibar, iron/ironing board, WiFi (free), bed sheets

10. Rodeway Inn

Rodeway Inn
Adams
United States
Brandie
CA $100
CA $112 total
includes taxes & fees
Oct 11 - Oct 12
Rodeway Inn
View all properties

Top Cheshire Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Great staff great restaurant!"
Michael 1-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Therooms were loud on the lower level."
Sheila 1-night trip
Posted 2 hours ago
Quality Inn Lee - Lenox South
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"The staff was extremely friendly. Did see several areas in the room that were dusty. Stains on the wallpaper and some wallpaper chipping off."
Frank 1-night trip
Posted 2 hours ago
Howard Johnson by Wyndham Lenox
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nasically a large motel with both an outdoor and indoor pool. A bit tired, but reasonably close to Lenox and to Tabglewood."
Jacob 1-night trip
Posted 17 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Great location for Mass Moca"
BONNIE 3-night trip
Posted 2 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.

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