Title: The Best Chester, MA Chalets from $74 | Expedia.com

[Chester Travel Guide](https://expedia.com/Chester.dx6005399)[Hotels in Chester](https://expedia.com/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6005399.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d6005399.Destination-Travel-Guides)

![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Chris Addams

![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Chester

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5754h3835x5y5-e38781aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking | Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-3661e0ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking, Kitchen (Larger Room, Sofabed, Full Kitchen) | Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/b5bac949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-c074381d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Baldwin Inn & Suites, SureStay Collection by Best Western

[](https://www.expedia.com/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information)

West Springfield

8.0/10

Very Good

(145 reviews)

"So close to the Big E Fairgroynds, wonderful service, would stay again!"

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

Terry

$101 nightly

$116 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms, Non Smoking | In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Great Barrington Berkshires

[](https://www.expedia.com/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information)

Great Barrington

7.6/10

Good

(574 reviews)

"Excellent location!!"

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

Abdul Samad

$75 nightly

$84 total

Mar 28 - Mar 29

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/aee2041b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Untold

[](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

Lenox

9.0/10

Wonderful

(881 reviews)

"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."

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

Payton

$78 nightly

$87 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom | Premium bedding, down comforters, pillowtop beds, individually furnished](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Element Lenox Berkshires

[](https://www.expedia.com/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information)

Lenox

9.6/10

Exceptional

(24 reviews)

"Friendly staff, beautiful interiors."

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

Izabela

$139 nightly

$155 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/83c805e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

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

### Best Western Plus Berkshire Hills Inn & Suites

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

Pittsfield

8.6/10

Excellent

(1,000 reviews)

"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "

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

Kristina

$107 nightly

$119 total

Mar 30 - Mar 31

Total with taxes and fees

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

![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 | Desk, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/c24971a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/47150b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Quality Inn Lee - Lenox South

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

Lee

8.4/10

Very Good

(1,001 reviews)

"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "

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

Amy

$76 nightly

$85 total

Apr 19 - Apr 20

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monument Mountain Motel

[](https://www.expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

Great Barrington

9.0/10

Wonderful

(835 reviews)

"Nice place and very reasonable for great location "

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

Raymond

$67 nightly

$74 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/a50fdd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, Multiple Beds | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/w863h648x1y0-4d00d4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/b8e5643f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, Multiple Beds | Bathroom | Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/1eae2c98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Valley Inn

[](https://www.expedia.com/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information)

West Hatfield

8.4/10

Very Good

(122 reviews)

"Friendly staff, really nice room, quiet. I really enjoyed my stay."

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

Desiree

$99 nightly

$111 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information)

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

![Indoor pool](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/07d4dc21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/13980508.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)

### TownePlace Suites by Marriott Hadley Amherst

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

Hadley

9.8/10

Exceptional

(75 reviews)

"The check in staff were amazing "

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

mandeep

$152 nightly

$170 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Front of property](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/cab085ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/efe975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive King Room | Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/4ae0b464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### D. Hotel Suites & Spa

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

Holyoke

9.4/10

Exceptional

(2,216 reviews)

"Very clean, comfortable, and quiet hotel. We enjoyed our visit."

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

Larry

$134 nightly

$149 total

Mar 30 - Mar 31

Total with taxes and fees

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

![View from property](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/2a79c048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/5b7eab2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/4592453d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/d0f01d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites Springfield Holyoke

[](https://www.expedia.com/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information)

Holyoke

9.2/10

Wonderful

(622 reviews)

"We enjoyed our 3 nights it was quiet and very clean "

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

Joanne

$118 nightly

$132 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information)

![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/aa01ab9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/8cf443f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/919a842d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room (Global Fusion) | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/8b862974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Naomi's Inn Bed & Breakfast

[](https://www.expedia.com/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information)

Liberty Heights

9.0/10

Wonderful

(430 reviews)

"So cute and accommodating to our schedule "

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

Carey Lynn

$105 nightly

$119 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/40e8ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/08190a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/f36d24b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/dffd5115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tru by Hilton Chicopee Springfield

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

Chicopee

9.0/10

Wonderful

(1,001 reviews)

"Best hotel in area."

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

William

$106 nightly

$120 total

Apr 7 - Apr 8

Total with taxes and fees

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

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

![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.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)

![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Mountain Lodge

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

Pittsfield

9.0/10

Wonderful

(888 reviews)

"Overall pleasant stay; great facilities, staff, and location"

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

Casey

$108 nightly

$120 total

Apr 26 - Apr 27

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/d09f8bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Accessible, Non Smoking | In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/65617a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/d26efba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business center](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/683c1f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn West Springfield

[](https://www.expedia.com/Springfield-Hotels-Hampton-Inn-West-Springfield.h21212.Hotel-Information)

West Springfield

8.2/10

Very Good

(1,003 reviews)

"Very good place to stay"

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

Gloria

$106 nightly

$121 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Springfield-Hotels-Hampton-Inn-West-Springfield.h21212.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.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)

![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286.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

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

Lenox

7.6/10

Good

(839 reviews)

"Staff was super nice! Everything was clean and neat. "

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

Elizabeth

$79 nightly

$88 total

Mar 28 - Mar 29

Total with taxes and fees

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

![Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/w4600h3096x0y4-086b73d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/35e3e6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/eda0b159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/0d525668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Westfield

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

Westfield

8.4/10

Very Good

(837 reviews)

"I"

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

Andrew

$110 nightly

$123 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

[](https://www.expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

Great Barrington

8.8/10

Excellent

(752 reviews)

"This is not my first stay. Great hotel to stay for ski trips "

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

Michael

$111 nightly

$124 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/279dc540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ef9bad04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Little Lion

[](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

Great Barrington

8.6/10

Excellent

(555 reviews)

"Clean … check in , good location for us .. we’ll be back in Maynn"

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

Kathleen

$110 nightly

$123 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

[](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

Lee

9.2/10

Wonderful

(1,001 reviews)

"Room was spotless, staff was very kind!"

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

Ilia

$94 nightly

$105 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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.

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## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Cottages

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Villas

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Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CONDO)

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## Top Chester Hotel Reviews

![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4_y.jpg)

### Tru by Hilton Chicopee Springfield

6/10 Okay

"The check in staff was not friendly or greet us upon arrival."

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

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg)

### D. Hotel Suites & Spa

10/10 Excellent

"Breakfast had good variety of choices. Staff were friendly and responsive. Hot tub and pool area was filled with adults and children the two time we considered going so not able to take advantage of that amenity."

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

![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/143e42a0_y.jpg)

### The Ellery

10/10 Excellent

"Great property with amazing staff. Close to Smith and in an historic area. Lots of great dining options, places to walk, close to everything. Easy check in and out, free parking, and good breakfast. "

[](https://expedia.com/Springfield-Hotels-The-Ellery.h892654.Hotel-Information)

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg)

### Berkshires Untold

10/10 Excellent

"Berkshires Untold is an old roadside motel that has been very spiffed up. The rooms are small but clean, comfortable, and nicely decorated and updated. Our bed was comfy with high end linens and a nice updated bathroom. The major drawback to the room is the very noisy HVAC unit. There's a super cozy, attractive lounge area and a charming little restaurant and bar. The menu is small but the food is quite good and having an onsite restaurant is convenient. The price we paid for a very off season Saturday night was excellent, but the rates really jack up during the summer Tanglewood season, far beyond what one would expect for a small motel room. The staff is friendly and professional, and dogs are welcome for an $85 fee. All in all, this is a very nice and sometimes very affordable Berkshires option. "

[](https://expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Room was comfortable and quiet. Staff accommodated a request to change rooms after check-in as we discovered there was someone next door who was constantly on the phone speaking loudly in a voice that carried on something business related. Relocating us was very appreciated."

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

![Baldwin Inn & Suites, SureStay Collection by Best Western](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-3661e0ca_y.jpg)

### Baldwin Inn & Suites, SureStay Collection by Best Western

10/10 Excellent

"Really nice "

[](https://expedia.com/Springfield-Hotels-Regency-Inn-Suites.h15705.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

"Excellent service. "

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

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"very clean and friendly staff"

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

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Great, neat, convoy my son. "

[](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

## Find out more about Chester

## Chester Chalets information

| Number of reviews | 14,152    |
| ----------------- | --------- |
| Accommodation     | 3 Chalets |
| Lowest Price      | $74       |
| Highest Price     | $155      |

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