Title: Book The Best Hotels in Chesterfield, MA for 2026 from CA $108 - Fully Refundable Options - Expedia.ca

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## Go beyond your typical stay in Chesterfield

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-20&d1=2026-02-20&endDate=2026-02-22&d2=2026-02-22&amenities=POOL)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-20&d1=2026-02-20&endDate=2026-02-22&d2=2026-02-22&amenities=PETS)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-20&d1=2026-02-20&endDate=2026-02-22&d2=2026-02-22&travelerType=family_friendly)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-20&d1=2026-02-20&endDate=2026-02-22&d2=2026-02-22&amenities=HOT_TUB)

Farm

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-20&d1=2026-02-20&endDate=2026-02-22&d2=2026-02-22&lodging=AGRITOURISM)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-20&d1=2026-02-20&endDate=2026-02-22&d2=2026-02-22&lodging=APARTMENT)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-20&d1=2026-02-20&endDate=2026-02-22&d2=2026-02-22&lodging=COTTAGE)

## Check prices for these dates

Tonight

[Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chesterfield hotels

![Front of property](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/b02dfcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/0bc486c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/fdc80b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/7d4b7b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blooming Inn

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information)

Shelburne Falls

9.2/10

Wonderful

(130 reviews)

"Beautiful comfortable home with many thoughtful touches"

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

Rachel

CA $123

CA $204 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/51285776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/d8217024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/532eb0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/5f79da29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Westfield - Springfield

[](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information)

Westfield

7.2/10

Good

(911 reviews)

"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."

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

Gloria

CA $119

CA $133 total

includes taxes & fees

Feb 27 - Feb 28

[](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/34065f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Refrigerator](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/04ad8e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/cde7c3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/241daa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Westfield

[](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.Hotel-Information)

Westfield

8.4/10

Very good

(825 reviews)

"I will stay again"

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

Jailene

CA $169

CA $189 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/f7391fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/bc7070b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/37c3c332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/be33985c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn on Boltwood

[](https://www.expedia.ca/Springfield-Hotels-Inn-On-Boltwood.h2027065.Hotel-Information)

Amherst

9.4/10

Exceptional

(762 reviews)

"It is a beautiful and historic property with an amazing restaurant and bar."

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

Kelly

CA $282

CA $315 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Springfield-Hotels-Inn-On-Boltwood.h2027065.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/dcc4e9f5.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/b2a572bd.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/w6714h4455x8y0-7f30ce4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Pittsfield

9.2/10

Wonderful

(81 reviews)

"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."

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

Laura Pearson

CA $181

CA $202 total

includes taxes & fees

Feb 26 - Feb 27

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

![37-inch LCD TV with cable channels, TV, iPod dock](https://images.trvl-media.com/lodging/1000000/490000/480800/480785/6c251969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/1000000/490000/480800/480785/60af1c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/490000/480800/480785/a53eec54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/490000/480800/480785/f5ba1cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel UMass

[](https://www.expedia.ca/Springfield-Hotels-Hotel-UMass.h480785.Hotel-Information)

Amherst

8.8/10

Excellent

(1,003 reviews)

"Great stay "

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

Kyle

CA $172

CA $193 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Springfield-Hotels-Hotel-UMass.h480785.Hotel-Information)

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/27ba18f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/b6081d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/bba60f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/59bbbbcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Lenox Pittsfield

[](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information)

Pittsfield

9.2/10

Wonderful

(665 reviews)

" Nice staff - beautiful hotel!"

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

MARY

CA $186

CA $208 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658945/978d1151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658945/31f9c61f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658945/eb368ec3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658945/498552ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Hadley Amherst

[](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-Hadley-Amherst.h1658945.Hotel-Information)

Hadley

9.0/10

Wonderful

(690 reviews)

"My son and I stayed during a big snow storm, staff not only got us checked in early but were super friendly and helpful. Hotel was also relatively spotless and clean given the circumstances with the storm."

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

William

CA $195

CA $218 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-Hadley-Amherst.h1658945.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/34000000/33240000/33232900/33232831/1c8d1bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/34000000/33240000/33232900/33232831/6a82b362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33240000/33232900/33232831/d135e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/34000000/33240000/33232900/33232831/388c68a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Homewood Suites by Hilton Hadley Amherst

[](https://www.expedia.ca/Springfield-Hotels-Homewood-Suites-By-Hilton-Hadley-Amherst.h33232831.Hotel-Information)

Hadley

9.4/10

Exceptional

(729 reviews)

"The room was efficient, clean and spacious. The pool was great and so was the breakfast. "

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

Julianne

CA $191

CA $214 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Springfield-Hotels-Homewood-Suites-By-Hilton-Hadley-Amherst.h33232831.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e57afaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e65bd9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library Suite, 1 King Bed](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c5c7040f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel On North

[](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

Pittsfield

9.6/10

Exceptional

(821 reviews)

"Great staff, beautiful hotel. Would definitely recommend "

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

Shawn

CA $204

CA $228 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343727/a2bd31ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343727/a1bbe5d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343727/73617262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343727/21bc83a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Elm Motel

[](https://www.expedia.ca/Springfield-Hotels-Elm-Motel.h1343727.Hotel-Information)

Westfield

7.2/10

Good

(123 reviews)

"Very clean, lacking bathroom and bathroom storage. Good price."

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

Daniel

CA $136

CA $152 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Springfield-Hotels-Elm-Motel.h1343727.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1220000/1217900/1217805/17a3ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One King Bed, Non-Smoking](https://images.trvl-media.com/lodging/2000000/1220000/1217900/1217805/202d865b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1220000/1217900/1217805/3908ae38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 7 AM to 9 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1220000/1217900/1217805/8ea065e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Hadley-Amherst Area

[](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Hadley-Amherst-Area.h1217805.Hotel-Information)

Hadley

9.0/10

Wonderful

(975 reviews)

"Best hotel in the area, hands down"

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

alexander

CA $169

CA $188 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Hadley-Amherst-Area.h1217805.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/a093eeea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e4c803ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Central Downtown Inn & Suites

[](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

Pittsfield

8.6/10

Excellent

(355 reviews)

"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."

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

Lynn

CA $138

CA $154 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/465e60d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Mountain Lodge

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

Pittsfield

9.0/10

Wonderful

(828 reviews)

"Very comfortable and very close to ski slope and restaurants"

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

Frederick

CA $135

CA $182 total

includes taxes & fees

Feb 8 - Feb 9

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

![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/107000000/106120000/106114100/106114099/ab4ff31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Quadruple Room, 2 Queen Beds | Living area](https://images.trvl-media.com/lodging/107000000/106120000/106114100/106114099/8797adfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/107000000/106120000/106114100/106114099/b58e5c14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Quadruple Room, 2 Queen Beds](https://images.trvl-media.com/lodging/107000000/106120000/106114100/106114099/d9139b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Black Walnut Inn

[](https://www.expedia.ca/Amherst-Hotels-Black-Walnut-Inn.h106114099.Hotel-Information)

North Amherst

9.8/10

Exceptional

(102 reviews)

"Enjoyable stay with a warm environment. Enjoyed the breakfast which was well prepared based on my order choice and request. Would stay again!"

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

Karri

[](https://www.expedia.ca/Amherst-Hotels-Black-Walnut-Inn.h106114099.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/5bcca6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![28-inch TV with digital channels, Netflix, pay movies](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/0db93a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/2bb92acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/d0afa322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Trail in Adams - Berkshires’ Art Hotel

[](https://www.expedia.ca/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information)

Adams

9.0/10

Wonderful

(144 reviews)

"Staff was great, very clean, Breakfast was terrific"

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

michael

CA $238

CA $265 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/13980508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/w4000h2663x0y4-2923be4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/cb762de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/w4000h2665x0y2-3046acd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### TownePlace Suites by Marriott Hadley Amherst

[](https://www.expedia.ca/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.Hotel-Information)

Hadley

9.8/10

Exceptional

(62 reviews)

"The property is very clean and pet friendly. The staff were very friendly and professional. I will definitely stay here again."

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

Diana

CA $203

CA $227 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b138d836.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)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/de2ab5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Accessible](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/644deeee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Inn

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

Pittsfield

7.8/10

Good

(842 reviews)

"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 $115

CA $129 total

includes taxes & fees

Mar 9 - Mar 10

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

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/bb79982b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, Private Bathroom (Field of Dreams)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/903dd1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harbour House Inn

[](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information)

Cheshire

9.4/10

Exceptional

(53 reviews)

"Nice place for a weekend away."

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

Gregory

CA $279

CA $295 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/e88abd9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

Pittsfield

8.0/10

Very good

(1,001 reviews)

"Staff was very courteous and rooms clean."

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

Steven

CA $139

CA $156 total

includes taxes & fees

Mar 7 - Mar 8

[](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-20&endDate=2026-02-21&regionId=89029&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## Stay near popular Chesterfield attractions

### Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621532666609)

### Krug Sugarbush

You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=909392809247760384)

### Chesterfield Public Library

Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=909393830101508096)

### Chesterfield Town Hall

After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=909392010971025408)

### Chesterfield Gorge Reservation

You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops. 

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=909393238931439616)

## Top Chesterfield Hotel Reviews

![Hotel UMass](https://images.trvl-media.com/lodging/1000000/490000/480800/480785/4e423f91_y.jpg)

### Hotel UMass

10/10 Excellent

"Great "

[](https://expedia.ca/Springfield-Hotels-Hotel-UMass.h480785.Hotel-Information)

![Fairfield Inn & Suites Springfield Northampton/Amherst](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c_y.jpg)

### Fairfield Inn & Suites Springfield Northampton/Amherst

10/10 Excellent

"Gorgeous room amazing stay"

[](https://expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being so cold out. The hotel is well maintained. The only small complaint I had was that the bathroom in our room needs to be refreshed. We have already started talking about coming back in the warmer weather to enjoy some of the outdoor activities in in the area."

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

![Quality Inn & Suites Northampton - Amherst](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269_y.jpg)

### Quality Inn & Suites Northampton - Amherst

10/10 Excellent

"Great room, very clean and welcoming, helpful staff. Breakfast was pretty good too!"

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information)

![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg)

### Tru by Hilton Chicopee Springfield

10/10 Excellent

"Friendly clean accommodation were just what we needed. "

[](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information)

![Comfort Inn & Suites](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/d1319a54_y.jpg)

### Comfort Inn & Suites

10/10 Excellent

"Clean room, friendly staff, "

[](https://expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information)

![Hotel Northampton](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/fe4b5272_y.jpg)

### Hotel Northampton

10/10 Excellent

"The staff were amazing and the room was perfect. "

[](https://expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information)

![Courtyard by Marriott Hadley Amherst](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658945/978d1151_y.jpg)

### Courtyard by Marriott Hadley Amherst

10/10 Excellent

"Great hotel to stay in. Staff is super friendly and pays attention to a details. Rooms are kept fresh and clean. I will return in future"

[](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-Hadley-Amherst.h1658945.Hotel-Information)

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg)

### D. Hotel Suites & Spa

10/10 Excellent

"Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back "

[](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information)

## More cheap stays in Chesterfield

![Riverdale Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459711/28e65efc_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Riverdale Inn

1500 Riverdale Street West Springfield MA

CA $94

CA $108 total

Feb 22 - Feb 23

includes taxes & fees

5.8/10 (1,001 reviews)

[](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-West-SpringfieldRoute-5.h459711.Hotel-Information)

![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn West Springfield

1150 Riverdale St West Springfield MA

CA $113

CA $130 total

Feb 12 - Feb 13

includes taxes & fees

7/10 Good! (1,001 reviews)

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information)

![Red Roof Inn PLUS+ West Springfield](https://images.trvl-media.com/lodging/1000000/30000/27100/27090/23b7c14f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street West Springfield MA

CA $116

CA $132 total

Feb 22 - Feb 23

includes taxes & fees

6.8/10 (1,002 reviews)

[](https://expedia.ca/Springfield-Hotels-Red-Roof-Inn-PLUS-West-Springfield.h27090.Hotel-Information)

![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

CA $122

CA $136 total

Mar 1 - Mar 2

includes taxes & fees

7/10 Good! (1,003 reviews)

[](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information)

![Comfort Inn & Suites](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/d1319a54_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Comfort Inn & Suites

400 Russell St Hadley MA

CA $153

CA $171 total

Mar 8 - Mar 9

includes taxes & fees

9.2/10 Wonderful! (1,003 reviews)

[](https://expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information)

![Quality Inn & Suites Northampton - Amherst](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

CA $155

CA $174 total

Mar 1 - Mar 2

includes taxes & fees

7/10 Good! (1,000 reviews)

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information)

## Hotels in Chesterfield with star rating

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

1 properties

[](https://expedia.ca/4Star-Chesterfield-Hotels.s40-0-d89029.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

79 properties

[](https://expedia.ca/3Star-Chesterfield-Hotels.s30-0-d89029.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

69 properties

[](https://expedia.ca/2Star-Chesterfield-Hotels.s20-0-d89029.Travel-Guide-Filter-Hotels)

## Frequently asked questions

### When is the best time to go to Chesterfield?

> This period offers stunning natural beauty as the Berkshire Hills transform with vibrant fall foliage. The weather is typically crisp and pleasant, ideal for outdoor activities like hiking, scenic drives, and exploring the local area. You'll find fewer crowds compared to peak summer, allowing for a more relaxed experience.
> 
>   
> Couples looking for a romantic getaway will particularly enjoy Chesterfield in the autumn. The picturesque landscapes provide a beautiful backdrop for leisurely drives along Route 143 or walks through the Chesterfield Gorge. Many local inns and bed and breakfasts offer cosy amenities, great for a peaceful escape.
> 
>   
> For travellers interested in outdoor pursuits, the autumn weather is great for exploring the many hiking trails in the surrounding state forests, such as the Knightville Dam area. The cooler temperatures make for comfortable walking, and the changing leaves offer spectacular views.

### Can I cancel my hotel reservation on Expedia?

### How can I save on a Chesterfield hotel booking with Expedia?

### How much is the nightly rate at a Chesterfield hotel?

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- [Flights to Western Massachusetts ](https://www.expedia.ca/Cheap-Flights-To-Western-Massachusetts.d6234063.Travel-Guide-Flights)
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- [Williamsburg Vacations ](https://www.expedia.ca/Williamsburg.d175048.Destination-Travel-Guides)

- [Car rentals near Western Massachusetts ](https://www.expedia.ca/Car-Rentals-In-Western-Massachusetts.d6234063.Car-Rental-Guide)
- [First Car Rental Rental Cars in Goshen ](https://www.expedia.ca/First-Car-Rental-Car-Rentals-In-Goshen.d109585-c1107.Car-Rental-Guide-Suppliers)
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- [Book Hotels in Chesterfield on Expedia.com ](https://www.expedia.com/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)

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