Title: The Best Chester, MA Resorts from $64 | 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)

![An amazing keystone arch bridge!](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

Next weekend

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

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

In two months

[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)

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

## Recommended hotels in Chester

![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)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5754h3835x5y5-e38781aa.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

7.8/10

Good

(128 reviews)

"Clean room and very spacious, staff was friendly, i would only add a small dinning table to the room. "

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

Tomarie

$87 nightly

$100 total

Mar 15 - Mar 16

Total with taxes and fees

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

![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)

![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)

![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)

### 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

(1,001 reviews)

"Very friendly and good Breakfast."

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

Jesse

$112 nightly

$125 total

Mar 29 - Mar 30

Total with taxes and fees

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

![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

9.8/10

Exceptional

(22 reviews)

"Spotless rooms and the friendliest service at the front desk! "

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

Mary

$139 nightly

$155 total

Mar 18 - Mar 19

Total with taxes and fees

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

(830 reviews)

"The room was clean, and the staff was friendly and helpful. "

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

Damien

$67 nightly

$74 total

Mar 15 - Mar 16

Total with taxes and fees

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

![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)

![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)

![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

9.2/10

Wonderful

(2,226 reviews)

"Great service, clean & quiet rooms, and a solid breakfast to start the day"

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

Stephanie

$121 nightly

$135 total

Mar 15 - Mar 16

Total with taxes and fees

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

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/0f74ae3a.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

(1,004 reviews)

"Safe, clean rooms, decent breakfast "

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

Neil

$84 nightly

$94 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-Quality-Inn.h459706.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/108000000/107580000/107579600/107579521/9704ee61.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/b2e93f7c.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)

### River Valley Inn

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

West Hatfield

8.4/10

Very Good

(118 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

$100 nightly

$112 total

Mar 15 - Mar 16

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)

![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)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.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

(869 reviews)

"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "

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

Melissa

$95 nightly

$106 total

Mar 25 - Mar 26

Total with taxes and fees

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

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

![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

(73 reviews)

"Loved that I could bring my dog! Large comfortable room and friendly staff! Great stay"

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

Pauline

$158 nightly

$176 total

Mar 18 - Mar 19

Total with taxes and fees

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

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

![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/8cd694d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Room, 1 King Bed, Non Smoking, No Children Allowed | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yankee, Trademark Collection by Wyndham

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

Lenox

9.2/10

Wonderful

(1,016 reviews)

"Very friendly staff comfy beds!"

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

Giselle

$93 nightly

$103 total

Mar 19 - Mar 20

Total with taxes and fees

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

![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)

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

![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.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

(1,001 reviews)

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

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

Wayne

$59 nightly

$64 total

Mar 15 - Mar 16

Total with taxes and fees

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

![Lobby](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/dffd5115.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

(1,002 reviews)

"Friendly clean accommodation were just what we needed. "

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

Carrie

$106 nightly

$120 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/a76d0174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Double Beds, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/e4ed4dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/1b7a7c58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/2f3875b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Springfield West Inn

[](https://www.expedia.com/Springfield-Hotels-Best-Western-Springfield-West-Inn.h14144.Hotel-Information)

West Springfield

7.8/10

Good

(1,002 reviews)

"The room was great and jose at the front desk was very kind amd helpful and at the breakfast department he was great."

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

LUIS

$88 nightly

$101 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Springfield-Hotels-Best-Western-Springfield-West-Inn.h14144.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)

![Suite, 1 Bedroom, Non Smoking | In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.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)

![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.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

(573 reviews)

"Excellent location!!"

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

Abdul Samad

$75 nightly

$84 total

Mar 15 - Mar 16

Total with taxes and fees

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

![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)

![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

(871 reviews)

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

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

Frederick

$115 nightly

$128 total

Apr 12 - Apr 13

Total with taxes and fees

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

![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)

![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)

![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/aa01ab9b.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

(429 reviews)

"Artful and inspiring interior decorating and delicious French toast for breakfast!"

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

Marielle

$101 nightly

$115 total

Mar 15 - Mar 16

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/1000000/900000/892300/892229/eb9d0598.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)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/dcdd836c.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)

### 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

(743 reviews)

"Great property, very accommodating. "

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

Shanice

$107 nightly

$120 total

Mar 15 - Mar 16

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)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.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)

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.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)

"Clean room, nice staff , decent breakfast. Overall a good stay . "

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

Anindita

$92 nightly

$103 total

Apr 6 - Apr 7

Total with taxes and fees

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

![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)

![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.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)

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

(838 reviews)

"Clean room and the bed was very comfortable "

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

Arlan

$79 nightly

$88 total

Mar 13 - Mar 14

Total with taxes and fees

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

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

![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

(618 reviews)

"Room was spotless, staff were nice. "

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

Jose I Medina

$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)

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

![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

8/10 Good

"Nice place to stay. Beautiful pond and lovely continental breakfast "

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

"Friendly, clean and comfortable. "

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

![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/27ce1034_y.jpg)

### Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Clean room, friendly and helpful staff. "

[](https://expedia.com/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information)

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

### Berkshire Mountain Lodge

10/10 Excellent

"the room was huge - we loved it!!"

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

"This has become our company's preferred hotel for business trips to the Holyoke/Northampton area. It is clean, quiet, safe, convenient, and the breakfast is stellar."

[](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

"The Ellery is a super comfortable simple and friendly hotel. It is ideal to visit your students at Smith College."

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

![Courtyard by Marriott West Springfield](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b_y.jpg)

### Courtyard by Marriott West Springfield

10/10 Excellent

"Clean and efficient. Great location to find a meal and get away from the Big E chaos."

[](https://expedia.com/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information)

![Blue – A Modern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2_y.jpg)

### Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent

"Highly recommend this was a beautiful hotel. The rooms were beautiful. The staff were so nice and I was so excited when I walked into the room and there was a massage chair."

[](https://expedia.com/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.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

"This area is really starting to build up. There is a small ski area. An Italian restaurant and 110 grill right on that road. About 15 min away Applebees. A lot of pizza and Mexican. Winter not only is there skiing there are a lot of snowmobile trails. Summer there are water falls you can see. Tubing you can do. The mountains are beautiful. Quiet and relaxing. "

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

## Find out more about Chester

## Chester Resorts information

| Number of reviews | 13,746    |
| ----------------- | --------- |
| Accommodation     | 4 Resorts |
| Lowest Price      | $64       |
| Highest Price     | $176      |

## 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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