Title: Chesterfield, MA Cottage Rentals  | Expedia.com

[Chesterfield Travel Guide](https://expedia.com/Chesterfield.dx89029)[Hotels in Chesterfield](https://expedia.com/Chesterfield-Hotels.d89029.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.com/Chesterfield-Vacation-Rentals.d89029.Travel-Guide-VacationRentals)[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

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=89029&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.com/Hotel-Search?regionId=89029&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.com/Hotel-Search?regionId=89029&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.com/Hotel-Search?regionId=89029&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 Chesterfield cottages

![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)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/539e07bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Charlemont

$515 nightly

$545 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.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=2026-04-08&endDate=2026-04-09&regionId=89029&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## 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=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CABIN)

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=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VACATION_HOME)

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=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=COTTAGE)

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=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CONDO)

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=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=APARTMENT)

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=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VILLA)

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=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CHALET)

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## Top Chesterfield Hotel Reviews

![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/143e42a0_y.jpg)

### The Ellery

10/10 Excellent

"Clean, friendly staff, quiet comfortable room and just enough breakfast to start my day. The stay worked out perfectly between travels. "

[](https://expedia.com/Springfield-Hotels-The-Ellery.h892654.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.com/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information)

![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4_y.jpg)

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

8/10 Good

"It’s ok."

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

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg)

### D. Hotel Suites & Spa

8/10 Good

"We spent a weekend at this hotel. To be honest, I think I was expecting a little better based on the strong reviews. The property was in decent shape but the rooms were incredibly sparse and basic: our bathroom shower curtain liner fell off repeatedly, no ventilation in there, room furniture was dated and basic, odd and lacking decor. It felt lower quality than our typical Hampton Inn. The breakfast was also only okay (not sure what the hype is), with terrible coffee, and the gym was incredibly hot and small, with limited equipment. I will say: the staff were friendly and helpful, and the common areas felt nice (the lobby, the pool, the breakfast nook, etc.). They also offer daily maid service which is unheard of anymore. The location was sort of odd but was close to the things we wanted to do (Northampton). I can't say I'd stay here again, unfortunately, though I do think it's a decent value if the price is right. "

[](https://expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.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.com/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.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![Fairfield Inn & Suites Springfield Holyoke](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/2a79c048_y.jpg)

### Fairfield Inn & Suites Springfield Holyoke

10/10 Excellent

"We enjoyed our 3 nights it was quiet and very clean "

[](https://expedia.com/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information)

![Candlewood Suites West Springfield by IHG](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/537cea4c_y.jpg)

### Candlewood Suites West Springfield by IHG

8/10 Good

"The staff is friendly and helpful. "

[](https://expedia.com/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.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

6/10 Okay

"Clean room. No conditioner in the shower and soap almost out. "

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

## Find out more about Chesterfield

## Chesterfield Cottages information

| Number of reviews |          |
| ----------------- | -------- |
| Accommodation     | Cottages |
| Lowest Price      |          |
| Highest Price     |          |

## Frequently asked questions

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