Title: Chester, MA Villas Rentals | 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)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[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 three months

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

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-06-05&endDate=2026-06-07&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/34000000/33300000/33298700/33298677/e09cf4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds | Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/8c645106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/e2688ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott West Springfield

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

West Springfield

9.2/10

Wonderful

(598 reviews)

"Nice and very clean hotel ! "

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

Morgan

$118 nightly

$135 total

Feb 12 - Feb 13

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/8801cfa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/4c6ff871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/dc04db42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cornell Inn, Lenox & The Berkshires

[](https://www.expedia.com/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information)

Lenox

9.0/10

Wonderful

(1,002 reviews)

"The Inn was very nice and the staff was super friendly and attentive."

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

Steven

$137 nightly

$154 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/6d051282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deep soaking bathtub](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/14870b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Double Room | Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/db3c3dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset Inn

[](https://www.expedia.com/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information)

Lee

7.6/10

Good

(411 reviews)

"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "

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

Kimberly

$95 nightly

$106 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information)

![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lakehouse Inn

[](https://www.expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information)

Lee

9.6/10

Exceptional

(292 reviews)

"A charming inn in the center of the Berkshires."

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

Danny

$142 nightly

$159 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.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)

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

![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)

### Howard Johnson by Wyndham Lenox

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

Lenox

7.6/10

Good

(830 reviews)

"Staff was very friendly and helpful."

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

Pamela

$65 nightly

$72 total

Feb 26 - Feb 27

Total with taxes and fees

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

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.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)

### 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

(731 reviews)

"Great property, very accommodating. "

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

Shanice

$107 nightly

$120 total

Feb 22 - Feb 23

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/e459ce18.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/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

9.0/10

Wonderful

(1,004 reviews)

"Room was clean and the staff was super friendly and helpful!"

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

Ethan

$95 nightly

$106 total

Feb 26 - Feb 27

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.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)

### Monument Mountain Motel

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

Great Barrington

9.0/10

Wonderful

(820 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

Feb 10 - Feb 11

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/67000000/66250000/66244800/66244754/f0d9797c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/047ef967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/28728ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/48ee1fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitlock

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

Lenox

8.6/10

Excellent

(286 reviews)

"Super cute place and walking distance to a bunch of great shops and food! "

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

Gina

$128 nightly

$143 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/dcb9c41b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/fc660f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/d47c2eca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Down comforters, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/a668b8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Chicopee/Springfield

[](https://www.expedia.com/Springfield-Hotels-Hampton-Inn-ChicopeeSpringfield.h892598.Hotel-Information)

Chicopee

9.0/10

Wonderful

(1,002 reviews)

"Clean comfortable rooms, great breakfast, very nice staff"

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

Edward

$107 nightly

$121 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Springfield-Hotels-Hampton-Inn-ChicopeeSpringfield.h892598.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/fa13e671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/94cb14a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4e4268ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Lion Inn

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

Stockbridge

8.8/10

Excellent

(1,003 reviews)

"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."

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

Gary

$185 nightly

$207 total

Mar 10 - Mar 11

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Villa, 3 Bedrooms | Iron/ironing board, free cribs/infant beds, WiFi, bed sheets](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/24f01653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Villa, 3 Bedrooms | Iron/ironing board, free cribs/infant beds, WiFi, bed sheets](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

[](https://www.expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

South Lee

9.0/10

Wonderful

(833 reviews)

"Great overnights stay, wish I was here longer "

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

Thomas

$130 nightly

$145 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.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)

![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)

![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)

"Safe, clean rooms, decent breakfast "

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

Neil

$84 nightly

$94 total

Feb 24 - Feb 25

Total with taxes and fees

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

![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)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.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

(854 reviews)

"So charming, clean, thoughtful touches and a really special place!"

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

Juliana

$98 nightly

$110 total

Mar 8 - Mar 9

Total with taxes and fees

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

(426 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

$103 nightly

$117 total

Feb 22 - Feb 23

Total with taxes and fees

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

![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/8dbc27a7.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/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

(553 reviews)

"Great friendly staff"

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

Pablo

$110 nightly

$123 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/34000000/33240000/33232900/33232831/858efd60.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)

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

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

### Homewood Suites by Hilton Hadley Amherst

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

Hadley

9.4/10

Exceptional

(730 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

$141 nightly

$158 total

Mar 2 - Mar 3

Total with taxes and fees

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

![View from property](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/5e996a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/w4000h2033x0y0-e62570a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/36a39838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/27ce1034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Lenox Berkshires

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

Lenox

9.2/10

Wonderful

(599 reviews)

"Our stay was great! "

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

Gianna

$130 nightly

$145 total

Mar 1 - Mar 2

Total with taxes and fees

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

![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)

![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)

### The Yankee, Trademark Collection by Wyndham

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

Lenox

9.2/10

Wonderful

(1,012 reviews)

"Very friendly staff comfy beds!"

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

Giselle

$92 nightly

$103 total

Feb 26 - Feb 27

Total with taxes and fees

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

![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/a856ec31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/eb4406db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/58d2b953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brook Farm Inn

[](https://www.expedia.com/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information)

Lenox

9.4/10

Exceptional

(164 reviews)

"Everything was perfect - location and accommodation."

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

Christopher

$191 nightly

$217 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Lenox-Hotels-Brook-Farm-Inn.h1196186.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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Apartments

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Villas

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VILLA)

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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CONDO)

Private vacation homes

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VACATION_HOME)

Cottages

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=COTTAGE)

Chalets

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CHALET)

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## Top Chester Hotel Reviews

![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

10/10 Excellent

"The staff was wonderful "

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

![Residence Inn by Marriott West Springfield](https://images.trvl-media.com/lodging/1000000/860000/852800/852716/fb4f9524_y.jpg)

### Residence Inn by Marriott West Springfield

10/10 Excellent

"Great friendly helpful staff, clean room and amenities "

[](https://expedia.com/Springfield-Hotels-Residence-Inn-By-Marriott-West-Springfield.h852716.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

"YES"

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

"The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay."

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

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"loved "

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

"Room was clean and nicely equipped with kitchen. Will return if the future. "

[](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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.com/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Springfield MA](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60_y.jpg)

### La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent

"I had a great night of sleep"

[](https://expedia.com/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information)

## Find out more about Chester

## Chester Villas information

| Number of reviews | 13,719   |
| ----------------- | -------- |
| Accommodation     | 2 Villas |
| Lowest Price      | $72      |
| Highest Price     | $217     |

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- [Becket Land Trust Historic Quarry ](https://www.expedia.com/Becket-Land-Trust-Historic-Quarry-Becket.d553248621532666600.Vacation-Attraction)
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