Title: Visit Cheshire: 2026 Travel Guide for Cheshire, Massachusetts | Expedia.com

[Hotels in Cheshire](https://expedia.com/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.com/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.com/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Car Rentals in Cheshire](https://expedia.com/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.com/Cheshire.d6005398.Destination-Travel-Guides)

# Cheshire, MA

## Travel Guide

![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/86318a94-cc98-4d4a-a83c-e012ece6ff66.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/81bbd72e-e9b3-4d05-ac68-b2406c65563e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..](https://images.trvl-media.com/place/6005398/5524f182-4aec-4e46-bab1-4eb1dd804bd0.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Cheshire Lake during a sunny winter day. ](https://images.trvl-media.com/place/6005398/bcaae993-192e-42dc-8569-9f9d02bcdcbe.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Cheshire

Things to do

- Cheshire Hotel Deals
- Vacation Rentals in Cheshire

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$126 nightly

$141 total

Mar 22 - Mar 23

Total with taxes and fees

Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...

8.8/10 Excellent! (2,305 reviews)

Hot tub and pool both clean and well maintained

Reviewed on Mar 15, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true&regionId=6005398)

![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/9903b094_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

$118 nightly

$132 total

Apr 5 - Apr 6

Total with taxes and fees

Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...

8.8/10 Excellent! (1,001 reviews)

For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options.

Reviewed on Mar 5, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true&regionId=6005398)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$115 nightly

$128 total

Apr 16 - Apr 17

Total with taxes and fees

Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...

9/10 Wonderful! (876 reviews)

Unbelievable’

Reviewed on Mar 15, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F16%2F2026&endDate=4%2F17%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true&regionId=6005398)

[See all 1,013 properties in Cheshire](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F18%2F2026&endDate=3%2F19%2F2026&regionId=6005398)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...

8.8/10 Excellent! (2,305 reviews)

Hot tub and pool both clean and well maintained

Reviewed on Mar 15, 2026

[](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Huttopia Berkshires 

312 Kittle Rd Williamstown MA

Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...

9.4/10 Exceptional! (10 reviews)

Excelente servicio

Reviewed on Mar 8, 2026

[](https://expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![The Ponds at Foxhollow](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Ponds at Foxhollow

3 Foxhollow Drive Route 7 Lenox MA

Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...

8.6/10 Excellent! (141 reviews)

I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ...

Reviewed on Feb 9, 2026

[](https://expedia.com/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

[See all properties in Cheshire](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=6005398&sort=VACATION_RENTAL)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

## Check Cheshire hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=2026-03-17&endDate=2026-03-18)[Mar 17 - Mar 18](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=2026-03-17&endDate=2026-03-18)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=2026-03-18&endDate=2026-03-19)[Mar 18 - Mar 19](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=2026-03-18&endDate=2026-03-19)

[This weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)

[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)

### Popular places to visit

#### St Mary's of the Assumption Church

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views, or seek out its ski slopes. 

[](https://expedia.com/St-Marys-Of-The-Assumption-Church-Cheshire.d553248621532665539.Vacation-Attraction)

## Cities near Cheshire

![Wahconah Falls in the Berkshires](https://images.trvl-media.com/place/6911/0d61b065-dfb2-41c6-8d5b-cded88165403.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Dalton

![Deer Hill Shelter is a backpackers shelter, and therefore FREE, unlike the other camp areas on Mt Greylock.  It's only about a mile and half from the parking area nearest to Campground Trail.  Deer Hill Trail itself branches off from Campground Trail to take you to the shelter.  Map location is approximate since it doesn't show all the trails and the shelter is dwarfed by the surrounding forest.  First come, first serve here ... and if you show up in the middle of the week in early summer, you might get it all to yourself like we did!](https://images.trvl-media.com/place/183333/ba4e7fc4-6985-4957-b20c-a1c15dc92f0e.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### New Ashford

![Main Street USA, North Adams, Massachusetts](https://images.trvl-media.com/place/6005393/cc755750-f4dd-4b43-9817-f53d7ef5c03c.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Adams

![WW2 Vetrans War Memorial Veterans War Memorial located in Lanesborough, MA The summit of Mt. Greylock](https://images.trvl-media.com/place/6005408/e6fe22ae-eb57-4b13-a5fa-fe1cb4a88ae8.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Lanesborough

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- [Hotels near St Mary's of the Assumption Church ](https://www.expedia.com/St-Marys-Of-The-Assumption-Church-Hotels.0-l553248621532665539-0.Travel-Guide-Filter-Hotels)
- [Hotels near Mount Greylock State Reservation Visitor Center ](https://www.expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels)
- [Lanesborough Hotels ](https://www.expedia.com/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels)
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- [4 Star Hotels in New Ashford ](https://www.expedia.com/4Star-New-Ashford-Hotels.s40-0-d183333.Travel-Guide-Filter-Hotels)
- [Adams Hotels ](https://www.expedia.com/Adams-Hotels.d6005393.Travel-Guide-Hotels)
- [B&B in Adams ](https://www.expedia.com/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Cottages in Adams ](https://www.expedia.com/Adams-Cottages.d6005393-aaCottages.Travel-Guide-Accommodation)
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- [Flights to Lanesborough ](https://www.expedia.com/Cheap-Flights-To-Lanesborough.d6005408.Travel-Guide-Flights)
- [Flights from Lanesborough ](https://www.expedia.com/lp/flights/6005408/flights-from-lanesborough)
- [Flights to Adams ](https://www.expedia.com/Cheap-Flights-To-Adams.d6005393.Travel-Guide-Flights)
- [Flights from Adams ](https://www.expedia.com/lp/flights/6005393/flights-from-adams)
- [Flights to Dalton ](https://www.expedia.com/Cheap-Flights-To-Dalton.d6911.Travel-Guide-Flights)
- [Flights to Hancock ](https://www.expedia.com/Cheap-Flights-To-Hancock.d112303.Travel-Guide-Flights)
- [Flights from Hancock ](https://www.expedia.com/lp/flights/112303/flights-from-hancock)

- [Mount Greylock State Reservation Visitor Center ](https://www.expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction)
- [Visit Lanesborough ](https://www.expedia.com/Lanesborough.dx6005408)
- [Visit New Ashford ](https://www.expedia.com/New-Ashford.dx183333)
- [Visit Adams ](https://www.expedia.com/Adams.dx6005393)
- [Susan B. Anthony Birthplace Museum ](https://www.expedia.com/Susan-B-Anthony-Birthplace-Museum-Adams.d553248621532666696.Vacation-Attraction)
- [East Hoosac Quaker Meetinghouse ](https://www.expedia.com/East-Hoosac-Quaker-Meetinghouse-Adams.d553248621561173644.Vacation-Attraction)
- [Adams Vacations ](https://www.expedia.com/Adams.d6005393.Destination-Travel-Guides)
- [Mount Greylock ](https://www.expedia.com/Mount-Greylock-Adams.d6091829.Vacation-Attraction)
- [Visit Hancock ](https://www.expedia.com/Hancock.dx112303)
- [Visit Dalton ](https://www.expedia.com/Dalton.dx6911)
- [Wahconah Falls State Park ](https://www.expedia.com/Wahconah-Falls-State-Park-Dalton.d553248621532665297.Vacation-Attraction)
- [Dalton Vacations ](https://www.expedia.com/Dalton.d6911.Destination-Travel-Guides)
- [Hancock Vacations ](https://www.expedia.com/Hancock.d112303.Destination-Travel-Guides)

- [Car rentals near Lanesborough ](https://www.expedia.com/Car-Rentals-In-Lanesborough.d6005408.Car-Rental-Guide)
- [Car rentals near New Ashford ](https://www.expedia.com/Car-Rentals-In-New-Ashford.d183333.Car-Rental-Guide)
- [Car rentals near Adams ](https://www.expedia.com/Car-Rentals-In-Adams.d6005393.Car-Rental-Guide)
- [Car rentals near Dalton ](https://www.expedia.com/Car-Rentals-In-Dalton.d6911.Car-Rental-Guide)
- [Car rentals near Hancock ](https://www.expedia.com/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide)

- [Lanesborough Vacation Rentals ](https://www.expedia.com/Lanesborough-Vacation-Rentals.d6005408.Travel-Guide-VacationRentals)
- [Dalton Vacation Rentals ](https://www.expedia.com/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals)
- [Hancock Vacation Rentals ](https://www.expedia.com/Hancock-Vacation-Rentals.d112303.Travel-Guide-VacationRentals)

- Cities near Cheshire
- Places of interest

[Dalton](https://expedia.com/Dalton.dx6911)[New Ashford](https://expedia.com/New-Ashford.dx183333)[Adams](https://expedia.com/Adams.dx6005393)[Lanesborough](https://expedia.com/Lanesborough.dx6005408)[Savoy](https://expedia.com/Savoy.dx6005417)[Windsor](https://expedia.com/Windsor.dx6005427)

- [Tanglewood Music Center ](https://expedia.com/Tanglewood-Music-Center-Lenox.d503292.Vacation-Attraction)
- [Jiminy Peak Mountain Resort ](https://expedia.com/Jiminy-Peak-Mountain-Resort-Hancock.d553248621532665536.Vacation-Attraction)
- [National Shrine of the Divine Mercy ](https://expedia.com/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction)
- [Williams College ](https://expedia.com/Williams-College-Williamstown.d6091833.Vacation-Attraction)
- [Green Mountain National Forest ](https://expedia.com/Green-Mountain-National-Forest-Vermont.d6115904.Vacation-Attraction)
- [Norman Rockwell Museum ](https://expedia.com/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction)
- [Massachusetts Museum of Contemporary Art ](https://expedia.com/Massachusetts-Museum-Of-Contemporary-Art-North-Adams.d6091827.Vacation-Attraction)
- [Berkshire East Ski Resort ](https://expedia.com/Berkshire-East-Ski-Resort-Charlemont.d553248621532666707.Vacation-Attraction)
- [Bousquet Ski Area ](https://expedia.com/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction)
- [The Clark Art Institute ](https://expedia.com/The-Clark-Art-Institute-Williamstown.d553248621533116688.Vacation-Attraction)
- [Lee Premium Outlets ](https://expedia.com/Lee-Premium-Outlets-Lee.d6127084.Vacation-Attraction)
- [The Mount ](https://expedia.com/The-Mount-Lenox.d553248621532665265.Vacation-Attraction)
- [Hancock Shaker Village ](https://expedia.com/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction)
- [Mount Greylock ](https://expedia.com/Mount-Greylock-Adams.d6091829.Vacation-Attraction)
- [Jacob's Pillow ](https://expedia.com/Jacobs-Pillow-Becket.d553248621532666599.Vacation-Attraction)
- [Naumkeag Museum ](https://expedia.com/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction)
- [Williamstown Theatre Festival ](https://expedia.com/Williamstown-Theatre-Festival-Williamstown.d553248621532665542.Vacation-Attraction)
- [Ventfort Hall Mansion and Gilded Age Museum ](https://expedia.com/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction)
- [Lenox Library ](https://expedia.com/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction)
- [Berkshire Museum ](https://expedia.com/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction)
- [Berkshire Botanical Garden ](https://expedia.com/Berkshire-Botanical-Garden-Stockbridge.d553248621532665247.Vacation-Attraction)
- [Deerfield River ](https://expedia.com/Deerfield-River-United-States-of-America.d682156682122641408.Vacation-Attraction)
- [Natural Bridge State Park ](https://expedia.com/Natural-Bridge-State-Park-North-Adams.d553248621560926711.Vacation-Attraction)
- [Wyndhurst Golf & Club ](https://expedia.com/Wyndhurst-Golf-Club-Lenox.d553248621532665266.Vacation-Attraction)
- [Bridge of Flowers ](https://expedia.com/Bridge-Of-Flowers-Shelburne-Falls.d553248621532666724.Vacation-Attraction)
- [Taconic Golf Club ](https://expedia.com/Taconic-Golf-Club-Williamstown.d553248621561173642.Vacation-Attraction)
- [Mount Greylock State Reservation Visitor Center ](https://expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction)
- [Berkshire Scenic Railway Museum ](https://expedia.com/Berkshire-Scenic-Railway-Museum-Massachusetts.d553248621532665275.Vacation-Attraction)
- [Grafton Lakes State Park ](https://expedia.com/Grafton-Lakes-State-Park-New-York.d6173181.Vacation-Attraction)

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