Title: 2 Stars Hotels in Cheshire, Massachusetts from CA $87 - Find Cheap Cheshire Hotels With 2 Stars | Expedia.ca

  

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# 2 Stars Hotels in Cheshire, Massachusetts from CA $87

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## Check availability on Cheshire 2 Star Hotels

Tonight

[Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-29&endDate=2025-10-30&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-30&endDate=2025-10-31&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Cheshire 2 Star Hotels

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/5a6f7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Howard Johnson by Wyndham Lenox

Lenox

7.6/10

Good

(816)

"Staff was very friendly and helpful."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pamela

CA $110

CA $123 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yankee, Trademark Collection by Wyndham

Lenox

9.0/10

Wonderful

(1022)

"Fresh breakfast menu, clean and great location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gail

CA $149

CA $167 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

8.6/10

Excellent

(1022)

"I have stayed here many times and it is consistently a comfortable, clean and quiet place."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeanine

CA $136

CA $152 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/b5e2455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/05418243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn

Lee

8.4/10

Very good

(1004)

"Staff was very helpful - easy location - clean rooms!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen

CA $129

CA $144 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/3ed5d9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/bd64a090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c2037034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FairBridge Inn Express

Pittsfield

5.4/10

(799)

"Good service and people"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jerod

CA $94

CA $105 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/e55e7242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/ceca8706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One King Bed, Non-Smoking, Accessible | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/5d049cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Berkshires-Lenox

Lenox

9.2/10

Wonderful

(1000)

"The staff is very friendly and helpful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

karin

CA $155

CA $173 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/f5e7ded9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/ddd4b2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/962c72ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mountain view](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/15afb24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Howard Johnson by Wyndham Williamstown

Williamstown

6.6/10

(897)

"Great affordable place to stay while in the northern Berkshires."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

PAUL

CA $119

CA $132 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Williamstown-Hotels-Howard-Johnson-By-Wyndham-Williamstown.h1498642.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/adb513b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/dd484194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5e45920f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Williamstown

Williamstown

8.8/10

Excellent

(389)

"our stay was great."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

nathaniel

CA $199

CA $223 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/617da859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/67e1adab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

9.4/10

Exceptional

(55)

"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marti

CA $177

CA $197 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/c3ce1b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/c07737f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/8f954601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Inn

Pittsfield

7.8/10

Good

(835)

"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

MARIA J

CA $107

CA $120 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/a5e72142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/w1290h860x0y968-0dd10b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/7549d558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/75e29869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Willows Motel Williamstown

Williamstown

9.0/10

Wonderful

(975)

"Br and rooms were cleaneakfast was excellent"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph

CA $124

CA $139 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information)

![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/0fb6095c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/b0a99b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/f0e5252a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/f9deb77e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Econo Lodge Lee - Great Barrington

Lee

6.4/10

(643)

"Staff friendly, room was quiet, large and comfortable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Barbara

CA $86

CA $96 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/caece0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/5062d555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Corner Motel

Williamstown

9.2/10

Wonderful

(877)

"Very nice staff, nice breakfast"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kerri

CA $104

CA $123 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/45e111cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/6203d3bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/488c62c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/568a1b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Villager Motel

Williamstown

8.8/10

Excellent

(753)

"It's very good for stay over"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Frances

CA $105

CA $117 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information)

![Courtyard](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/69831a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/d7f7feed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/5e670f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/d5a67b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Springs Motel

New Ashford

9.2/10

Wonderful

(83)

"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer

CA $143

CA $157 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/8337d62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Queen](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/fbf7e370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, free WiFi, bed sheets](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/0a525567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitlock

Lenox

8.6/10

Excellent

(277)

"great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brian

CA $174

CA $194 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/3e40d6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/8e0c73d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/f6ede23a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Williamstown Motel

Williamstown

9.4/10

Exceptional

(309)

"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

DAVID

CA $135

CA $151 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/126ab2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/4d496801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/bf0ac5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/beaa7d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Travel Lodge

Austerlitz

5.4/10

(456)

"The parking is right in front of the cabin the breakfast is made to order, very nice place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William

CA $95

CA $107 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Albany-Hotels-Berkshire-Travel-Lodge.h1793522.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/9b821fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/2558ee66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/bb325877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pleasant Valley Motel West Stockbridge

West Stockbridge

6.8/10

(1001)

"good average place to stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Terry

CA $79

CA $87 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/b03b8d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/19cf619f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/25529e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/d7e3ccf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pilgrim Inn

Lee

5.8/10

(330)

"Was horrible. Unsafe and scarey"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sharon

CA $103

CA $116 total

includes taxes & fees

Nov 7 - Nov 8

[](https://www.expedia.ca/Lee-Hotels-Pilgrim-Inn.h49177721.Hotel-Information)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

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## Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Cheshire.

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

CA $99

CA $126 total

Nov 9 - Nov 10

includes taxes & fees

8.6/10 Excellent! (2,106 reviews)

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

![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hotel Downstreet, an Ascend Collection Hotel

40 Main St, North Adams, MA

CA $211

CA $236 total

Nov 9 - Nov 10

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

[](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

CA $115

CA $159 total

Nov 2 - Nov 3

includes taxes & fees

9/10 Wonderful! (737 reviews)

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Cheshire.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&regionId=6005398&star=20)

You can also use these popular filters to refine your search.

[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&regionId=6005398&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&regionId=6005398&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&regionId=6005398&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&regionId=6005398&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&regionId=6005398&star=20&star=20&amenities=WATER_PARK)

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.

## Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.

[See all hotels in Cheshire](https://www.expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&adults=2&regionId=6005398)

![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=899&h=675&p=1&q=high)

Photo by Ed Gaffny

## Top Cheshire Hotel Reviews

![Howard Johnson by Wyndham Lenox](//images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg)

### Howard Johnson by Wyndham Lenox

10/10 Excellent

"Coffee maker looks like it has mold inside "

[](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information)

## Find out more about Cheshire

Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Cheshire, Cheshire you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions.

Several of the best hotels with 2 Stars in Cheshire are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. You won’t believe how inexpensive your next vacation can be when you settle in at a top two star hotel in Cheshire.

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