Title: Chesterfield Vacation Rentals from $201: Search Short-Term Rentals | Expedia.com

[Chesterfield Travel Guide](https://expedia.com/Chesterfield.dx89029)[Hotels in Chesterfield](https://expedia.com/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Flights to Chesterfield](https://expedia.com/Cheap-Flights-To-Chesterfield.d89029.Travel-Guide-Flights)[Car Rentals in Chesterfield](https://expedia.com/Car-Rentals-In-Chesterfield.d89029.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.com/Chesterfield.d89029.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=89029&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chesterfield vacation rentals

![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)

![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111942700/111942669/1b404b44.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)

![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

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

Holyoke

9.8/10

Exceptional

(14 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.

$328 nightly

$366 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/4626de59.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)

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/35000000/34090000/34080200/34080135/b2f467ca.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.com/Easthampton-Hotels-The-Creation-Station-Is-A-Cozy-Place-So-Make-Yourself-At-Home.h34080135.Hotel-Information)

Easthampton Ma.

10/10

Exceptional

(73 reviews)

"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "

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

Connie P.

$248 nightly

$277 total

Mar 9 - Mar 10

Total with taxes and fees

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

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

![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/c8db5a9a.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)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/512b2604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely 2nd Floor Apartment

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

Greenfield

10/10

Exceptional

(49 reviews)

"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "

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

Geoffrey B.

$180 nightly

$201 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112520000/112517100/112517070/4ef23803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112520000/112517100/112517070/41b13ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/113000000/112520000/112517100/112517070/3daf052e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112520000/112517100/112517070/f3111c8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

[](https://www.expedia.com/Amherst-Hotels-CLOSE-To-DowntownUMASS-Condo-With-Game-Room-Big-Backyard.h112517070.Hotel-Information)

Amherst

9.0/10

Wonderful

(20 reviews)

"Great property! Thank you for a wonderful stay."

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

David

$377 nightly

$421 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Amherst-Hotels-CLOSE-To-DowntownUMASS-Condo-With-Game-Room-Big-Backyard.h112517070.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)

![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)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110170000/110169900/110169858/9fd49d85.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)

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

[](https://www.expedia.com/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.

$339 nightly

$385 total

Mar 15 - Mar 16

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/f63afa55.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)

![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.com/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information)

Russell

10/10

Exceptional

(143 reviews)

"Perfect spot for a family celebration!"

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

Kerry P.

$321 nightly

$339 total

Mar 6 - Mar 7

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h599x0y41-cd278b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w508h683x258y0-18d1cb27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/4e9408e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h490x0y96-4fcb5611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bear Creek Cabin

[](https://www.expedia.com/Charlemont-Hotels-Bear-Creek-Cabin.h91621591.Hotel-Information)

Charlemont

10/10

Exceptional

(46 reviews)

"We enjoyed our stay!!"

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

Hillary S.

$426 nightly

$476 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-Bear-Creek-Cabin.h91621591.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/c077bee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/212e023d.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/b4b598c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Colrain Spring into Adventure HotTub AirHockey Firepit

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

Colrain

9.8/10

Exceptional

(47 reviews)

"Great house for family gatherings "

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

John Paul B.

$576 nightly

$644 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/ed6f8836.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)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/a233230f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Valley View Post & Beam Villa!

[](https://www.expedia.com/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.

$789 nightly

$881 total

Mar 16 - Mar 17

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/a462abe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/b8092849.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)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/bab6261b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Retreat inAmherst

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

Amherst

10/10

Exceptional

(1 review)

"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

$752 nightly

$840 total

Mar 8 - Mar 9

Total with taxes and fees

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

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/6065c0a3.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)

### Button's Modern Luxury Walkup Downtown Northampton

[](https://www.expedia.com/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

$540 nightly

$603 total

Mar 8 - Mar 9

Total with taxes and fees

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

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

![Interior](https://images.trvl-media.com/lodging/112000000/111910000/111900200/111900181/5d91e664.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)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111910000/111900200/111900181/388ab578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Amherst

10/10

Exceptional

(9 reviews)

"Perfect location, clean house, great for families with kids!"

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

Emily Robustelli K.

$819 nightly

$915 total

Mar 8 - Mar 9

Total with taxes and fees

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

![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)

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

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

[](https://www.expedia.com/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.

$512 nightly

$572 total

Mar 30 - Mar 31

Total with taxes and fees

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

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

![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/c8b2ae4a.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)

### Treetop Hideaway in Tyringham

[](https://www.expedia.com/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.

$526 nightly

$556 total

Mar 11 - Mar 12

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8425e45e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/a2f8cee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2281e60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

[](https://www.expedia.com/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.

$353 nightly

$395 total

Mar 12 - Mar 13

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/2f78aa12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/08591748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/20e7ddaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121910000/121902900/121902882/04847bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charlemont Chalet - A 15 Acre Private Retreat

[](https://www.expedia.com/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information)

Charlemont

$605 nightly

$653 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-Charlemont-Chalet-Where-The-Mountains-Meet-Luxury.h121902882.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/528fbc22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/a296b140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/1c2ae12d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/7e305bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

[](https://www.expedia.com/Becket-Hotels-Secluded-Sophistication-In-The-Berkshires-49-Acres-Of-Quiet-Luxury-In-Becket.h120275326.Hotel-Information)

Becket

10/10

Exceptional

(1 review)

"Beautiful home, attentive host. Location is as peaceful as can be. "

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

Rick M.

$571 nightly

$638 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Becket-Hotels-Secluded-Sophistication-In-The-Berkshires-49-Acres-Of-Quiet-Luxury-In-Becket.h120275326.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/125000000/124280000/124273200/124273112/bd43511e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124280000/124273200/124273112/6ba55a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124280000/124273200/124273112/243a2493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124280000/124273200/124273112/6712b9ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 2-bedroom cottage on Robert Frost Trail

[](https://www.expedia.com/Amherst-Hotels-Beautiful-2-Bedroom-Cottage-On-Robert-Frost-Trail.h124273112.Hotel-Information)

Amherst

$237 nightly

$265 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Amherst-Hotels-Beautiful-2-Bedroom-Cottage-On-Robert-Frost-Trail.h124273112.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)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/037efde9.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)

### Riverbend Berkshire East Basecamp - 3 bedrooms available

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

Charlemont

10/10

Exceptional

(2 reviews)

"Very nice house and the stay was unproblematic!"

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

Noah K.

$395 nightly

$441 total

Mar 5 - Mar 6

Total with taxes and fees

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/9f36ff80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/d523ca40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/fc000043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122230000/122227300/122227227/8d6ee530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat

[](https://www.expedia.com/Charlemont-Hotels-1920s-Inspired-Spacious-5-Bedroom-Home-Minutes-To-Berkshire-East.h122227227.Hotel-Information)

Charlemont

10/10

Exceptional

(2 reviews)

"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "

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

Jason F.

$576 nightly

$643 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-1920s-Inspired-Spacious-5-Bedroom-Home-Minutes-To-Berkshire-East.h122227227.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.com/Hotel-Search?startDate=2026-03-18&endDate=2026-03-19&regionId=89029&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CABIN)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VILLA)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=COTTAGE)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+Massachusetts%2C+United+States+of+America&regionId=89029&latLong=42.391754%2C-72.839821&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CHALET)

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## Top Chesterfield Hotel Reviews

![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

8/10 Good

"The gym didn’t have much machines or weights available. The parking was good but limited. The staff at the front desk were nice. However the bed sheets had a few blood stains and it did not look clean. "

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

6/10 Okay

"The first night was awful loud couldn’t sleep the people next door and across , had to sleep with my tv on 60 and still could hear at times paid for a tub accessible room and I thought when u pay to hold a room that’s the point but on the day of got a call that room wasn’t available, this was a staycation to soak a relax . Tub was the main idea . Other than that ya I enjoyed one day if that . "

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

![Comfort Inn & Suites Hadley - Amherst](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/f0e51cc3_y.jpg)

### Comfort Inn & Suites Hadley - Amherst

10/10 Excellent

"This is an excellent place to stay while in the Amherst/Hadley area. Convenient location, a friendly and welcoming team of staff, a complimentary breakfast (with some healthy options available) served every morning, a swimming pool, and plenty of space, both in the guest rooms as well as in the common areas of the lobby. I would definitely stay here again, and will recommend it to others."

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

![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/58b2bc45_y.jpg)

### Quality Inn West Springfield

8/10 Good

"The room was clean and comfortable - certainly met our needs, The staff was very accommodating - we arrived early and the front desk receptionist was able to check us in early. This was our second stay here in a few weeks and the receptionist remembered us and asked how we were (my husband had just had cataract surgery). The breakfast was a typical continental breakfast, which met our needs. Having the Japanese restaurant right there was nice. I expect that whenever we need a hotel room in West Springfield, we will choose to stay here."

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

![Courtyard by Marriott Hadley Amherst](https://images.trvl-media.com/lodging/2000000/1660000/1659000/1658945/978d1151_y.jpg)

### Courtyard by Marriott Hadley Amherst

10/10 Excellent

"Great service "

[](https://expedia.com/Springfield-Hotels-Courtyard-By-Marriott-Hadley-Amherst.h1658945.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

"This was one of th best hotel experiences I have ever had!!! The staff- Michael, Jayden, and Sadien were SUPER friendly and welcoming. They give you a little package of cookies, cracker, Doritos and water at check in. The room is beautiful and well appointed and very clean. The bed and linens are crisp and super comfortable and there are not enough great things I can say about the MASSAGE CHAIR!!!! We relaxed in it every chance we got! The hotel was very pretty, quiet, clean, and being able to make a hot latte and grab a muffin in the morning was amazing. The location is extremely convenient and quick to so many things - including MGM, which we were going to for a concert, and many eating establishments. I hope this hotel keeps "

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

"We received a warm welcome Waited just a few minutes for room to be ready Breakfast included with stay which is always a plus to get you on your way Enough parking for all"

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

8/10 Good

"Stayed here because I was having the floors in my house redone everything was clean crispy everything worked no problems with that but I don’t know if there was a generator or the heating air ducts that were allowed enough that I left the TV on at night and the TV must collect some kind of satellite or something but it kept clicking off whatever station it was on and would be down for a minute or two and come back on I’ll be watching your show it would go blue and then come back on when I got up in the morning I was in the elevator and somebody else was saying the same thing to me but overall everything was clean brand new or at least up-to-date "

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

![Inn on Boltwood](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/f7391fc0_y.jpg)

### Inn on Boltwood

8/10 Good

"Lovely stay!"

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

## Find out more about Chesterfield

**Everything you need to know about Chesterfield vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chesterfield vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $201 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chesterfield rentals**

At Expedia, we put the best Chesterfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Chesterfield ](https://expedia.com/Chesterfield-Private-Vacation-Homes.d89029-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Chesterfield ](https://expedia.com/Chesterfield-Apartments.d89029-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Chesterfield ](https://expedia.com/Chesterfield-Cottages.d89029-aaCottages.Travel-Guide-Accommodation)
- [Farmstay in Chesterfield ](https://expedia.com/Chesterfield-Agritourism.d89029-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Chesterfield ](https://expedia.com/Chesterfield-Motels.d89029-aaMotels.Travel-Guide-Accommodation)
- [B&B in Chesterfield ](https://expedia.com/Chesterfield-Bed-And-Breakfast.d89029-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Chesterfield ](https://expedia.com/Chesterfield-Cabins.d89029-aaCabins.Travel-Guide-Accommodation)
- [Guest Houses in Chesterfield ](https://expedia.com/Chesterfield-Guest-Houses.d89029-aaGuestHouses.Travel-Guide-Accommodation)
- [Condo Rentals in Chesterfield ](https://expedia.com/Chesterfield-Condos.d89029-aaCondos.Travel-Guide-Accommodation)
- [Chalets in Chesterfield ](https://expedia.com/Chesterfield-Chalets.d89029-aaChalets.Travel-Guide-Accommodation)
- [Lodges in Chesterfield ](https://expedia.com/Chesterfield-Lodges.d89029-aaLodges.Travel-Guide-Accommodation)
- [Resorts in Chesterfield ](https://expedia.com/Chesterfield-Resorts.d89029-aaResorts.Travel-Guide-Accommodation)
- [Villas in Chesterfield ](https://expedia.com/Chesterfield-Villas.d89029-aaVillas.Travel-Guide-Accommodation)
- [Castles in Chesterfield ](https://expedia.com/Chesterfield-Castles.d89029-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Chesterfield?

### What are some of the best vacation rentals in Chesterfield?

### What’s there to see and do in Chesterfield?

### What’s a vacation rental in Chesterfield like?

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## Go further with the Expedia app

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