Title: Chesterfield Vacation Home Rentals from CA $282: Search Top Private Vacation Homes for Rent | Expedia.ca

 

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# Chesterfield Vacation Rentals

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## Check prices for these dates

Next weekend

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=89029&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Chesterfield Vacation Homes

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/271afff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/d4ae0376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### Cozy Home in Holyoke with 3 bedrooms

Holyoke

9.6/10

Exceptional

(10)

"We stayed in Holyoke as my daughter was performing at UMASS Amherst and this was a great location only 25 minutes of so away from campus. The home is spacious with two bedrooms and bathrooms. A very clean and well maintained the home. Would definitely recommend and will visit again!! "

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

Carrie M.

CA $182

CA $454 total

includes taxes & fees

Nov 18 - Nov 19

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

![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/79a253e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/70342e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/d695e72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely 2nd Floor Apartment

Greenfield

10/10

Exceptional

(44)

"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."

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

Wendy M.

CA $163

CA $282 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/abcd3f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/138b1f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/e6df39fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114880000/114878300/114878238/w5278h3491x0y0-d48a63f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in the Woods

Russell

10/10

Exceptional

(3)

"Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!"

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

Jennifer F.

CA $237

CA $451 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Westfield-Hotels-Home-In-The-Woods.h114878238.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/77e07421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest

10/10

Exceptional

(4)

"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"

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

James F.

CA $204

CA $529 total

includes taxes & fees

Nov 18 - Nov 19

[](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/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)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/73d09dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, music library, video library](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/d59ece13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Easthampton Ma.

10/10

Exceptional

(70)

"A very short but a really fun stay. Great location to just relax and get away from it all."

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

Naseem P.

CA $252

CA $390 total

includes taxes & fees

Nov 20 - Nov 21

[](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/111000000/110170000/110169900/110169858/f01b2eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/7d179dad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/4a6be0fe.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)

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

Chicopee

10/10

Exceptional

(11)

"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."

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

Matt G.

CA $252

CA $539 total

includes taxes & fees

Nov 18 - Nov 19

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2278baae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/80124d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/347359ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest

9.6/10

Exceptional

(10)

"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."

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

James D.

CA $225

CA $550 total

includes taxes & fees

Nov 18 - Nov 19

[](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/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/af5c0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0e82b119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/508c5b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big farmhouse in the foothills of the Berkshires

Russell

10/10

Exceptional

(143)

"We enjoyed our stay in this beautiful old farmhouse. Plenty of room for everyone and kitchen and linens were fully stocked."

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

Nicole K.

CA $216

CA $436 total

includes taxes & fees

Nov 18 - Nov 19

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74440000/74431000/74430957/ddba05d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74440000/74431000/74430957/c5092ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74440000/74431000/74430957/4800b3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74440000/74431000/74430957/d926c08d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Granby

9.4/10

Exceptional

(18)

"Clean and easy to check in. Nick was easy to communicate with."

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

Jeff M.

CA $208

CA $374 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Granby-Hotels-Quiet-3-BR-15-Bath-Duplex-Near-5-Colleges.h74430957.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/78692cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/d5f8e878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/4702110d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/a2e76ef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Couples 2 Bedroom Retreat-Close to Shelburne Falls

Colrain

10/10

Exceptional

(4)

"We had everything we needed for a fun and relaxing family get away. We loved how close it was to great restaurants and activities like rafting, zip lining, and the mountain coaster. The kitchen is fully stocked and everything was clean and well organized.Erica and Casey were great hosts and so helpful in answering any and all of our questions before check in. We will definitely be back! "

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

Heather B.

CA $238

CA $522 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Colrain-Hotels-Couples-2-Bedroom-Retreat-Hot-Tub-Air-Hockey-Close-To-ShelburneFalls.h113519074.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/458d1d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/8fcd0ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/eb8c4f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/w2988h3984x23y25-6b991349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FaLL Western Mass Getaway-Airhockey-Firepit

Colrain

9.8/10

Exceptional

(38)

"Couldn’t have been happier with our stay. The space was absolutely perfect for our large family, and the owners couldn’t have been nicer or more helpful. Phenomenal kitchen space (love the island!). Can’t wait to stay here again!"

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

Taylor C.

CA $386

CA $883 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122420000/122414000/122413946/w1316h878x2y2-5fcc2e9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122420000/122414000/122413946/1183d1cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122420000/122414000/122413946/w1318h875x1y2-cbfb416d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/123000000/122420000/122414000/122413946/w1316h879x2y3-65b770cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Welcoming 3-bedroom house- Gardner home

Chicopee

CA $168

CA $474 total

includes taxes & fees

Nov 19 - Nov 20

[](https://www.expedia.ca/Chicopee-Hotels-Welcoming-3-Bedroom-House-Gardner-Home.h122413946.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.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)

![Interior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/adca2c72.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)

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

Pittsfield

7.8/10

Good

(6)

"Very clean and spacious! We enjoyed our stay with our small pup!"

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

Ann C.

CA $377

CA $689 total

includes taxes & fees

Nov 18 - Nov 19

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

![Dining](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/dfb5a38b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/1cd53f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/4bf012a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/e110ab89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Retreat inAmherst

Amherst

10/10

Exceptional

(1)

"Very helpful and easy communication. Very clean and nice place. We were very busy and only really were at the place to sleep but it is quiet and perfect for a restful stay."

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

Robert

CA $757

CA $1,175 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Amherst-Hotels-Luxury-Retreat-InAmherst.h112643986.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/f305b62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/597105fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/d80b29aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/76291106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

CA $224

CA $580 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/329257ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a7b21f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a0287de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/e73088a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bungalow in the Berkshires

Lee

10/10

Exceptional

(4)

"Great location, very clean and well appointed with everyth"

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

Nick R.

CA $386

CA $540 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Lee-Hotels-Bungalow-In-The-Berkshires.h111821595.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121670000/121668900/121668821/1c881c8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121670000/121668900/121668821/d641fcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121670000/121668900/121668821/393ac0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121670000/121668900/121668821/5a0f852a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Deerfield Treasure!

Deerfield

CA $626

CA $752 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Deerfield-Hotels-Old-Deerfield-Treasure.h121668821.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111910000/111900200/111900181/723a7787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111910000/111900200/111900181/453b337d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/112000000/111910000/111900200/111900181/dcd925fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111910000/111900200/111900181/f374747d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Amherst

10/10

Exceptional

(8)

"My family and I stayed here while moving our daughter in to UMass. The home was so lovely and clean. It had so many extra touches throughout the house. Everything you could want and need! Thank you to our wonderful hosts. We will absolutely stay here again. "

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

Carmella C.

CA $1,401

CA $2,279 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Amherst-Hotels-Spacious-5-Bedroom-Home-With-Game-Room-In-Amherst-Mins-To-UMass.h111900181.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/c038a4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/e8577fe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/1163baa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/b87b098e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charlemont Chalet - A 15 Acre Private Retreat

Charlemont

CA $515

CA $939 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-01&endDate=2025-12-02&regionId=89029&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=APARTMENT)

Cabins

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=VILLA)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=VACATION_HOME)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-02-15&d1=2026-02-15&endDate=2026-02-18&d2=2026-02-18&lodging=CHALET)

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## Top Chesterfield Hotel Reviews

### Quality Inn West Springfield

10/10 Excellent

"Very courteous staff. Comfortable, clean room. Always interesting people travelling through."

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information)

### Berkshire Mountain Lodge

10/10 Excellent

"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "

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

### Red Roof Inn PLUS+ South Deerfield – Amherst

10/10 Excellent

"Stop over hotel "

[](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information)

### Comfort Inn & Suites

10/10 Excellent

"The room was clean and comfortable. The bed and pillows were wonderful. The breakfast wasn’t the typical beige breakfast. There were waffles, muffins, yogurt, fresh fruit, cereal, sausage, ham, coffee, etc. I would stay there again. "

[](https://expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information)

### Hotel UMass

10/10 Excellent

"Great on campus location!"

[](https://expedia.ca/Springfield-Hotels-Hotel-UMass.h480785.Hotel-Information)

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

10/10 Excellent

"The staff were awesome! Both ladies at the front desk were so nice and accommodating. Would definitely stay there again!"

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

### The Ellery

10/10 Excellent

"I stayed in a double queen room with my daughter on a visit to Smith. The room was very comfortable, the host was delightful l, and the breakfast was delicious! Will be back!"

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

### Inn on Boltwood

10/10 Excellent

"Excellent "

[](https://expedia.ca/Springfield-Hotels-Inn-On-Boltwood.h2027065.Hotel-Information)

### Homewood Suites by Hilton Hadley Amherst

10/10 Excellent

"Really good place to go "

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

## Find out more about Chesterfield

## Chesterfield Vacation Homes information

| Number of reviews | 366 |
| --- | --- |
| Accommodation | 144 Vacation Homes |
| Lowest Price | CA $282 |
| Highest Price | CA $2,279 |

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