Title: Chester Vacation Rentals from CA $434: Short-Term Rentals for 2026 | Expedia.ca

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Photo by Chris Addams

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/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.ca/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.ca/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.ca/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)

## Our top choices for Chester vacation rentals

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/807b3960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/1c7057e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/22ef1826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

Sherwood Forest

9.8/10

Exceptional

(14 reviews)

"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"

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

Matthew F.

CA $221

CA $545 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/df22d08a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/8eda9941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/9f68233b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105670000/105660100/105660083/4a573ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Meadow Retreat

[](https://www.expedia.ca/Granby-Hotels-Peaceful-Meadow-Retreat.h105660083.Hotel-Information)

Granby

10/10

Exceptional

(18 reviews)

"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "

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

Kaleigh L.

CA $122

CA $247 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Granby-Hotels-Peaceful-Meadow-Retreat.h105660083.Hotel-Information)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/4626de59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/e43c1750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/08d859c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/e3cded0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Creation Station is a cozy place so make yourself at home.

[](https://www.expedia.ca/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.Hotel-Information)

Easthampton Ma.

10/10

Exceptional

(75 reviews)

"An amazing location with the most friendly host! My mom, dog and i absolutely enjoyed this spot. Perfect for a fall get away and would stay again."

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

Kelly Z.

CA $249

CA $384 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/3219fa05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/219f247f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/d1d1a287_edited_5b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/dead818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Home in Holyoke with 3 bedrooms

[](https://www.expedia.ca/Holyoke-Hotels-Cozy-Home-In-Holyoke-With-2-Bedrooms.h111942669.Hotel-Information)

Holyoke

9.8/10

Exceptional

(15 reviews)

"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."

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

Stacy G.

CA $227

CA $517 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Holyoke-Hotels-Cozy-Home-In-Holyoke-With-2-Bedrooms.h111942669.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/b924c628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/2350af4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0f27818f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big farmhouse in the foothills of the Berkshires

[](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

Russell

10/10

Exceptional

(144 reviews)

"The house is absolutely charming and cozy. It was very clean as well. "

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

Amanda C.

CA $276

CA $507 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/0e4076ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/c729995e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a133e616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

Sherwood Forest

10/10

Exceptional

(5 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

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

Sharon K.

CA $201

CA $520 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/w4000h2662x0y5-f1ed56ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/4fb8018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/0ab9f2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/7d4bb1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

[](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

Hinsdale

9.8/10

Exceptional

(36 reviews)

"Amazing, peaceful, immaculately clean property. "

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

Cec C.

CA $246

CA $610 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/111000000/110910000/110901900/110901825/af8c3db5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/111000000/110910000/110901900/110901825/ca0b095a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110910000/110901900/110901825/ed280229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110910000/110901900/110901825/194b8d06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Chicopee Getaway

[](https://www.expedia.ca/Chicopee-Hotels-Charming-Chicopee-Getaway.h110901825.Hotel-Information)

Chicopee

7.6/10

Good

(4 reviews)

"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "

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

Tamara S.

CA $140

CA $388 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Chicopee-Hotels-Charming-Chicopee-Getaway.h110901825.Hotel-Information)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/d5a3643f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/6f0714e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/e597dbad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/4b576c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse with Pool Table - Renovated w/ King Bed 

[](https://www.expedia.ca/Chicopee-Hotels-Townhouse-With-Pool-Table-Renovated-W-King-Bed.h110169858.Hotel-Information)

Chicopee

10/10

Exceptional

(12 reviews)

"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "

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

Tonya Z.

CA $249

CA $531 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Chicopee-Hotels-Townhouse-With-Pool-Table-Renovated-W-King-Bed.h110169858.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/ded0f208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/33f72fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/f2798a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/6b7aa883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Button's Modern Luxury Walkup Downtown Northampton

[](https://www.expedia.ca/Northampton-Hotels-Buttons-Modern-Luxury-Walkup-Downtown-Northampton.h117659835.Hotel-Information)

Northampton

10/10

Exceptional

(2 reviews)

"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"

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

AMY

CA $327

CA $679 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Northampton-Hotels-Buttons-Modern-Luxury-Walkup-Downtown-Northampton.h117659835.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/123000000/122420000/122413700/122413677/ae62138c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/123000000/122420000/122413700/122413677/3052fc5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122420000/122413700/122413677/b84ffea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122420000/122413700/122413677/17dcc3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom apartment in Chicopee

[](https://www.expedia.ca/Chicopee-Hotels-Cozy-2-Bedroom-Apartment-In-Chicopee.h122413677.Hotel-Information)

Chicopee

10/10

Exceptional

(3 reviews)

"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "

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

Christopher P.

CA $195

CA $285 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Chicopee-Hotels-Cozy-2-Bedroom-Apartment-In-Chicopee.h122413677.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Riverside Berkshires Retreat

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

Great Barrington

9.0/10

Wonderful

(12 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

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

Cristine C.

CA $280

CA $434 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information)

Pittsfield

7.8/10

Good

(7 reviews)

"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."

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

Liz V.

CA $372

CA $679 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/79e104d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/7a56f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/fc7d25b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/ed6f8836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Valley View Post & Beam Villa!

[](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information)

Whately

10/10

Exceptional

(8 reviews)

"Thanks for a great stay"

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

Andrea M.

CA $691

CA $872 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/5d56a155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/708e6bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/bee0b9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/c1c12e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 12-acre Vacation Rental in the Berkshires!

[](https://www.expedia.ca/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.Hotel-Information)

Charlemont

CA $336

CA $752 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b86b4635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk into town, soak up sun on enclosed porch & steps away from nature trails!

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

Stockbridge

10/10

Exceptional

(35 reviews)

"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"

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

Susan

CA $496

CA $1,003 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/e3f04cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/dc4b2063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/d96d2729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/129a2984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treetop Hideaway in Tyringham

[](https://www.expedia.ca/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information)

Monterey

9.0/10

Wonderful

(10 reviews)

"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"

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

Sarah B.

CA $365

CA $771 total

includes taxes & fees

Mar 30 - Mar 31

[](https://www.expedia.ca/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun Filled Lenox Retreat - Minutes to Tanglewood!

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

Lee

9.6/10

Exceptional

(5 reviews)

"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."

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

Paulo I.

CA $249

CA $633 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92010000/92006700/92006650/ab3fd377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92010000/92006700/92006650/a939343c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/93000000/92010000/92006700/92006650/e29416c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/93000000/92010000/92006700/92006650/7b43e03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic downtown house. Unscented products and sustainability practices.

[](https://www.expedia.ca/Northampton-Hotels-Renovated.h92006650.Hotel-Information)

Northampton

10/10

Exceptional

(7 reviews)

"The house was very comfortable and we enjoyed our visit very much "

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

Debbie L.

CA $580

CA $1,032 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/Northampton-Hotels-Renovated.h92006650.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

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Cottages

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Condos

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Private vacation homes

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## Top Chester Hotel Reviews

![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.ca/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.ca/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.ca/Lenox-Hotels-Yankee-Inn.h54944.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

"Staff was amazing! Rooms were spotless. "

[](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.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.ca/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information)

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

### Tru by Hilton Chicopee Springfield

10/10 Excellent

"Such a zen and peaceful place Just what I needed I’ll be back for sure And the staff are excellent also"

[](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.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.ca/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.ca/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.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

## Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Chester ](https://expedia.ca/Chester-Private-Vacation-Homes.d6005399-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Chester ](https://expedia.ca/Chester-Cottages.d6005399-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Chester ](https://expedia.ca/Chester-Apartments.d6005399-aaApartments.Travel-Guide-Accommodation)
- [B&B in Chester ](https://expedia.ca/Chester-Bed-And-Breakfast.d6005399-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Motels in Chester ](https://expedia.ca/Chester-Motels.d6005399-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Chester ](https://expedia.ca/Chester-Cabins.d6005399-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Chester ](https://expedia.ca/Chester-Agritourism.d6005399-aaAgritourism.Travel-Guide-Accommodation)
- [Condo Rentals in Chester ](https://expedia.ca/Chester-Condos.d6005399-aaCondos.Travel-Guide-Accommodation)
- [Guest Houses in Chester ](https://expedia.ca/Chester-Guest-Houses.d6005399-aaGuestHouses.Travel-Guide-Accommodation)
- [Resorts in Chester ](https://expedia.ca/Chester-Resort-Hotels.d6005399-aaResortHotels.Travel-Guide-Accommodation)
- [Inns in Chester ](https://expedia.ca/Chester-Inns.d6005399-aaInns.Travel-Guide-Accommodation)
- [Chalets in Chester ](https://expedia.ca/Chester-Chalets.d6005399-aaChalets.Travel-Guide-Accommodation)
- [Lodges in Chester ](https://expedia.ca/Chester-Lodges.d6005399-aaLodges.Travel-Guide-Accommodation)
- [Villas in Chester ](https://expedia.ca/Chester-Villas.d6005399-aaVillas.Travel-Guide-Accommodation)
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- [Castles in Chester ](https://expedia.ca/Chester-Castles.d6005399-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

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