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

![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/d239029a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

$136 nightly

$152 total

Apr 9 - Apr 10

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! (1,000 reviews)

Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ...

Reviewed on Mar 22, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%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

$121 nightly

$135 total

Mar 26 - Mar 27

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! (885 reviews)

very clean and friendly staff

Reviewed on Mar 24, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F26%2F2026&endDate=3%2F27%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true&regionId=6005398)

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Berkshires Untold

194 Pittsfield Rd Lenox MA

$78 nightly

$87 total

Mar 29 - Mar 30

Total with taxes and fees

Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...

9/10 Wonderful! (880 reviews)

Wonderful place, great toiletries and great friendly staff. We will be back

Reviewed on Mar 22, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=76297618&PinnedHotelID=76297618&HadPinnedHotel=true&regionId=6005398)

[See all 1,015 properties in Cheshire](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F26%2F2026&endDate=3%2F27%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.

![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)

![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Jiminy Peak Mountain Resort

37 Corey Rd Hancock MA

Book a stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...

[](https://expedia.com/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.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=2026-03-25&endDate=2026-03-26)[Mar 25 - Mar 26](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=2026-03-25&endDate=2026-03-26)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=2026-03-26&endDate=2026-03-27)[Mar 26 - Mar 27](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=2026-03-26&endDate=2026-03-27)

[This 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)

[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6005398&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)

### Popular places to visit

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

5/5(1 review)

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)
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- [Adams Hotels ](https://www.expedia.com/Adams-Hotels.d6005393.Travel-Guide-Hotels)
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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)
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- [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)
- [National Shrine of the Divine Mercy ](https://expedia.com/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction)
- [Jiminy Peak Mountain Resort ](https://expedia.com/Jiminy-Peak-Mountain-Resort-Hancock.d553248621532665536.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)
- [The Mount ](https://expedia.com/The-Mount-Lenox.d553248621532665265.Vacation-Attraction)
- [The Clark Art Institute ](https://expedia.com/The-Clark-Art-Institute-Williamstown.d553248621533116688.Vacation-Attraction)
- [Hancock Shaker Village ](https://expedia.com/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction)
- [Lee Premium Outlets ](https://expedia.com/Lee-Premium-Outlets-Lee.d6127084.Vacation-Attraction)
- [Jacob's Pillow ](https://expedia.com/Jacobs-Pillow-Becket.d553248621532666599.Vacation-Attraction)
- [Mount Greylock ](https://expedia.com/Mount-Greylock-Adams.d6091829.Vacation-Attraction)
- [Bousquet Ski Area ](https://expedia.com/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction)
- [Grafton Lakes State Park ](https://expedia.com/Grafton-Lakes-State-Park-New-York.d6173181.Vacation-Attraction)
- [Bridge of Flowers ](https://expedia.com/Bridge-Of-Flowers-Shelburne-Falls.d553248621532666724.Vacation-Attraction)
- [Williamstown Theatre Festival ](https://expedia.com/Williamstown-Theatre-Festival-Williamstown.d553248621532665542.Vacation-Attraction)
- [Deerfield River ](https://expedia.com/Deerfield-River-United-States-of-America.d682156682122641408.Vacation-Attraction)
- [Naumkeag Museum ](https://expedia.com/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction)
- [Wyndhurst Golf & Club ](https://expedia.com/Wyndhurst-Golf-Club-Lenox.d553248621532665266.Vacation-Attraction)
- [Berkshire Botanical Garden ](https://expedia.com/Berkshire-Botanical-Garden-Stockbridge.d553248621532665247.Vacation-Attraction)
- [Shakespeare and Company ](https://expedia.com/Shakespeare-And-Company-Lenox.d6127086.Vacation-Attraction)
- [Taconic Golf Club ](https://expedia.com/Taconic-Golf-Club-Williamstown.d553248621561173642.Vacation-Attraction)
- [Ventfort Hall Mansion and Gilded Age Museum ](https://expedia.com/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction)
- [Mount Greylock State Reservation Visitor Center ](https://expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction)
- [Natural Bridge State Park ](https://expedia.com/Natural-Bridge-State-Park-North-Adams.d553248621560926711.Vacation-Attraction)
- [Goose Pond Reservation ](https://expedia.com/Goose-Pond-Reservation-Lee.d6339855.Vacation-Attraction)
- [Berkshire Museum ](https://expedia.com/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction)
- [Harriman Reservoir ](https://expedia.com/Harriman-Reservoir-Vermont.d762079879267004416.Vacation-Attraction)

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