Title: The Best Chester, MA Resorts 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)

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## Check prices for these dates

Next weekend

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-06-05&endDate=2026-06-07&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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

## Recommended hotels in Chester

![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)

![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)

![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.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

(1,002 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

$123 nightly

$137 total

Apr 12 - Apr 13

Total with taxes and fees

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

![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/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)

![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

(838 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

Apr 9 - Apr 10

Total with taxes and fees

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

![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)

![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 | 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

8.6/10

Excellent

(127 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

$107 nightly

$119 total

Apr 21 - Apr 22

Total with taxes and fees

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

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

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.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)

### Berkshires Untold

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

Lenox

9.0/10

Wonderful

(889 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

$102 nightly

$114 total

Apr 8 - Apr 9

Total with taxes and fees

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

![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)

![Suite, 1 King Bed, Non Smoking, Kitchen (with Sofabed, Full Kitchen) | Private kitchenette | Microwave](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5753h3840x5y0-8e399dec.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)

![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)

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

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

West Springfield

7.8/10

Good

(159 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 14 - Apr 15

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.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)

![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)

![Studio Suite | Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/12b5137a.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

(2,231 reviews)

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

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

Larry

$150 nightly

$168 total

Apr 8 - Apr 9

Total with taxes and fees

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

![Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.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

$108 nightly

$120 total

Apr 26 - Apr 27

Total with taxes and fees

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

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

![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.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)

### Element Lenox Berkshires

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

Lenox

9.6/10

Exceptional

(25 reviews)

"Friendly staff, beautiful interiors."

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

Izabela

$143 nightly

$160 total

Apr 14 - Apr 15

Total with taxes and fees

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

![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)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/07d4dc21.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

(76 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 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.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 | Desk, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.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)

![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)

### Quality Inn Lee - Lenox South

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

Lee

8.4/10

Very Good

(1,000 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

$93 nightly

$104 total

Apr 26 - Apr 27

Total with taxes and fees

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

![Room (Louis XIV) | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/9e954e9a.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/a4915f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mort's Library | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/f25262f1.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

(431 reviews)

"Breakfast was exceptional. We couldn’t have been happier during our stay."

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

Robert

$112 nightly

$127 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.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)

![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)

### Berkshire Mountain Lodge

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

Pittsfield

9.0/10

Wonderful

(895 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

May 7 - May 8

Total with taxes and fees

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

![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](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/cdf64ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Point of interest](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/390a52f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pleasant Valley Motel West Stockbridge

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

West Stockbridge

6.8/10

(1,002 reviews)

"Priced very reasonably and the room was clean and comfy!"

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

Wayne

$71 nightly

$78 total

Apr 8 - Apr 9

Total with taxes and fees

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

![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)

![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.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

(575 reviews)

"Excellent location!!"

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

Abdul Samad

$75 nightly

$84 total

Apr 8 - Apr 9

Total with taxes and fees

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

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

![Fitness facility](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/6ea50f48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business center](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/w4598h3100x2y0-5384346d.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/c5af3791.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

(840 reviews)

"We had an excellent experience all around. "

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

Jennifer

$118 nightly

$132 total

Apr 19 - Apr 20

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

(754 reviews)

"Staff was great! Clean room, parking was always available. Breakfast was great. Had a great time!"

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

Brigid

$115 nightly

$128 total

Apr 20 - Apr 21

Total with taxes and fees

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

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

![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)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.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

9.0/10

Wonderful

(1,003 reviews)

"Room was spotless, staff was very kind!"

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

Ilia

$100 nightly

$112 total

Apr 19 - Apr 20

Total with taxes and fees

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

![Lobby](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4.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)

![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)

### Tru by Hilton Chicopee Springfield

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

Chicopee

9.0/10

Wonderful

(1,004 reviews)

"Best hotel in area."

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

William

$106 nightly

$120 total

Apr 20 - Apr 21

Total with taxes and fees

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

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

![Reception](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/c682c6c9.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)

### Fairfield Inn & Suites Springfield Holyoke

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

Holyoke

9.2/10

Wonderful

(625 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

Apr 20 - Apr 21

Total with taxes and fees

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

![Business center](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/afa8b6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking | Pillowtop beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118896/5f79da29.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)

### Quality Inn Westfield - Springfield

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

Westfield

7.2/10

Good

(919 reviews)

"Everything clean "

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

GLADYS

$93 nightly

$104 total

May 3 - May 4

Total with taxes and fees

[](https://www.expedia.com/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.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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## Top Chester Hotel Reviews

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

### D. Hotel Suites & Spa

8/10 Good

"I personally loved everything about the hotel. You walked in and it was very clean and the staff was super friendly and very informative. The room was very clean and spacious and the Wi-Fi was fast and there was no buffering. The breakfast was really nice and yummy. There were free, orange juice and 24 hour hot chocolate and coffee which I liked. The hot tub was amazing on my joints and in the hot tub. There was a view of the window that faced the sun so you can see the sunset from inside. The TV channels were nice there is Family Guy or South Park or Futurama to watch if you’re bored. I kinda hoped that there was YouTube on the TV but that’s OK. There is a stove top and a sink and a fridge for you to use which I thought was really neat. And it came with plates and silverware and glasses that you could use and wash which I thought was so nice. My only complaint was that the air conditioner was controlled by the wall thermostat and for some reason it would not cool down the setting would either only allow to turn it on or off or heat. There was no cooling option except for a fan. There was no fan in the bathroom, but that’s OK."

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

![Candlewood Suites West Springfield by IHG](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/537cea4c_y.jpg)

### Candlewood Suites West Springfield by IHG

10/10 Excellent

"This was a great place. Clean and the staff was friendly and welcoming "

[](https://expedia.com/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.Hotel-Information)

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

### Berkshires Untold

10/10 Excellent

"for a stay it was perfect. The layout is motel style but the design and care for the place elevates the stay exponentially. Cosmetically the rooms are gorgeous and the lobby is stunning. "

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

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

### The Ellery

10/10 Excellent

"Close to the Smith campus and downtown Northampton. A great place to stay."

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"Love that place. Does need a little sprucing up. Staff great and accomodating "

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

6/10 Okay

"Minimal breakfast choices. Staff was helpful but place was a little run down. Was clean though and served its purose. Across from fair grounds and close to good restaurants. "

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

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

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

6/10 Okay

"Great dinner, nice room. Only complaint is that none of the 3 elevators would come to the 6 floor in the morning. It was a long walk with our baggage."

[](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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

"Breakfast was fine. Orange juice though was just orange colored water"

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

![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130_y.jpg)

### The Red Lion Inn

10/10 Excellent

"What a beautiful, unique building. Full of antiques and feels like going back in time. The ride up to my fourth floor room in the 19th century cage elevator was a wonderful touch. Can’t wait to go back again. "

[](https://expedia.com/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

## Find out more about Chester

## Chester Resorts information

| Number of reviews | 13,950    |
| ----------------- | --------- |
| Accommodation     | 4 Resorts |
| Lowest Price      | $74       |
| Highest Price     | $170      |

## Frequently asked questions

### What is Chester like for a resort vacation?

### What's the best resort for my stay in Chester?

### What can I do in Chester?

### What's the weather like in Chester?

### What's the best way to get to and around Chester?

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