Title: Visit Chesterfield: 2026 Travel Guide for Chesterfield, Massachusetts | Expedia.com

[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)

# Chesterfield, MA

## Travel Guide

## Visit Chesterfield

Things to do

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=DX_SPRING_PROMO_89029)

- Chesterfield Hotel Deals
- Vacation Rentals in Chesterfield

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

$121 nightly

$135 total

Mar 9 - Mar 10

Total with taxes and fees

Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...

9.4/10 Exceptional! (2,216 reviews)

Older property with quirk and charm. Enjoyed our stay very much.

Reviewed on Mar 5, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&selected=849303&PinnedHotelID=849303&HadPinnedHotel=true&regionId=89029)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$115 nightly

$128 total

Apr 5 - Apr 6

Total with taxes and fees

Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...

9/10 Wonderful! (869 reviews)

The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after ...

Reviewed on Mar 6, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true&regionId=89029)

![Comfort Inn & Suites Hadley - Amherst](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/f0e51cc3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Comfort Inn & Suites Hadley - Amherst

400 Russell St Hadley MA

$109 nightly

$121 total

Mar 22 - Mar 23

Total with taxes and fees

Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

9.2/10 Wonderful! (1,008 reviews)

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 ...

Reviewed on Mar 3, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=558078&PinnedHotelID=558078&HadPinnedHotel=true&regionId=89029)

[See all 514 properties in Chesterfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F7%2F2026&endDate=3%2F8%2F2026&regionId=89029)

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.

![Peace and quiet on the lake](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/2959f9e4_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Peace and quiet on the lake

 Becket MA

Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...

9.6/10 Exceptional! (234 reviews)

Host was great! Quick communication. Place is a gem for peace and tranquility! The home is beautiful with great view.

Reviewed on Feb 18, 2026

[](https://expedia.com/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information)

![Elm Suite with a Private Bathroom in front of Smith College Quadrangle](https://images.trvl-media.com/lodging/77000000/76670000/76663400/76663304/w527h682x257y1-cbfd4b54_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Elm Suite with a Private Bathroom in front of Smith College Quadrangle

 Northampton MA

Stay at this apartment in Northampton. Enjoy in-room jetted tubs, an in-room coffeemaker, and air conditioning. Popular attractions Smith College Botanic Garden ...

9.8/10 Exceptional! (26 reviews)

Our stay here was amazing! The host was great about checking in and was super responsive. The room is quaint and cozy. The bathtub was perfect for a romantic weekend getaway. We both have back problems and the bed was comfortable and we both woke up pain free. We will definitely be back! Thanks for ...

Reviewed on Mar 1, 2026

[](https://expedia.com/Northampton-Hotels-Elm-Suite-With-A-Private-Bathroom-In-Front-Of-Smith-College-Quadrangle.h76663304.Hotel-Information)

![Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/b918ded9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

 Lanesborough MA

Stay at this vacation home in Lanesborough. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...

10/10 Exceptional! (12 reviews)

The house had all we needed and we enjoyed the stay very much. Lots of room and amenities with soap, toothpaste, plenty of towels, plenty of kitchen utensils and spices. Great service too! Adam tested the bbq when we arrived and determined it wasn’t working so he brought us a new one an hour later! ...

Reviewed on Feb 22, 2026

[](https://expedia.com/Lanesborough-Hotels-Cozy-Lake-House-With-Hot-Tub-Enjoy-Everything-The-Berkshires-Have-To-Offer.h95207502.Hotel-Information)

[See all properties in Chesterfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=89029&sort=VACATION_RENTAL)

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.

## Check Chesterfield hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89029&startDate=2026-03-06&endDate=2026-03-07)[Mar 6 - Mar 7](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89029&startDate=2026-03-06&endDate=2026-03-07)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89029&startDate=2026-03-07&endDate=2026-03-08)[Mar 7 - Mar 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89029&startDate=2026-03-07&endDate=2026-03-08)

[This weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89029&startDate=3%2F6%2F2026&endDate=3%2F8%2F2026)[Mar 6 - Mar 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=89029&startDate=3%2F6%2F2026&endDate=3%2F8%2F2026)

### Popular places to visit

#### Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area. 

[](https://expedia.com/Chesterfield-Gorge-Chesterfield.d553248621532666609.Vacation-Attraction)

#### Chesterfield Public Library

Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops. 

[](https://expedia.com/Chesterfield-Public-Library-Chesterfield.d909393830101508096.Vacation-Attraction)

#### Krug Sugarbush

You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops. 

[](https://expedia.com/Krug-Sugarbush-Chesterfield.d909392809247760384.Vacation-Attraction)

## Cities near Chesterfield

![Beautiful waterfalls nestled away in the countryside. ](https://images.trvl-media.com/place/132966/5e95a670-722b-45e6-8d54-96fabaf4303c.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Huntington

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- [Greenmotion Rental Cars in Western Massachusetts ](https://www.expedia.com/Greenmotion-Car-Rentals-In-Western-Massachusetts.d6234063-c1093.Car-Rental-Guide-Suppliers)
- [National Car Rental Rental Cars in Western Massachusetts ](https://www.expedia.com/National-Car-Rental-Car-Rentals-In-Western-Massachusetts.d6234063-c42.Car-Rental-Guide-Suppliers)
- [Budget Rental Cars in Western Massachusetts ](https://www.expedia.com/Budget-Car-Rentals-In-Western-Massachusetts.d6234063-c39.Car-Rental-Guide-Suppliers)
- [Car rentals near Goshen ](https://www.expedia.com/Car-Rentals-In-Goshen.d109585.Car-Rental-Guide)
- [Car rentals near Worthington ](https://www.expedia.com/Car-Rentals-In-Worthington.d6005428.Car-Rental-Guide)
- [Car rentals near Cummington ](https://www.expedia.com/Car-Rentals-In-Cummington.d183324.Car-Rental-Guide)

- [Western Massachusetts Vacation Rentals ](https://www.expedia.com/Western-Massachusetts-Vacation-Rentals.d6234063.Travel-Guide-VacationRentals)
- [Cummington Vacation Rentals ](https://www.expedia.com/Cummington-Vacation-Rentals.d183324.Travel-Guide-VacationRentals)

- Cities near Chesterfield
- Places of interest

[Cummington](https://expedia.com/Cummington.dx183324)[Huntington](https://expedia.com/Huntington.dx6005407)[Worthington](https://expedia.com/Worthington.dx6005428)

- [Chesterfield Gorge ](https://expedia.com/Chesterfield-Gorge-Chesterfield.d553248621532666609.Vacation-Attraction)
- [University of Massachusetts Amherst ](https://expedia.com/University-Of-Massachusetts-Amherst-Amherst.d6091819.Vacation-Attraction)
- [Amherst College ](https://expedia.com/Amherst-College-Amherst.d6085401.Vacation-Attraction)
- [Big E ](https://expedia.com/Big-E-West-Springfield.d553248621533116953.Vacation-Attraction)
- [Smith College ](https://expedia.com/Smith-College-Northampton.d6315876.Vacation-Attraction)
- [Mount Holyoke College ](https://expedia.com/Mount-Holyoke-College-South-Hadley.d6092307.Vacation-Attraction)
- [Berkshire East Ski Resort ](https://expedia.com/Berkshire-East-Ski-Resort-Charlemont.d553248621532666707.Vacation-Attraction)
- [Holyoke Mall ](https://expedia.com/Holyoke-Mall-Holyoke.d503293.Vacation-Attraction)
- [Hampshire College ](https://expedia.com/Hampshire-College-Massachusetts.d6085406.Vacation-Attraction)
- [Connecticut River ](https://expedia.com/Connecticut-River-United-States-of-America.d553248621555565605.Vacation-Attraction)
- [Jacob's Pillow ](https://expedia.com/Jacobs-Pillow-Becket.d553248621532666599.Vacation-Attraction)
- [Lee Premium Outlets ](https://expedia.com/Lee-Premium-Outlets-Lee.d6127084.Vacation-Attraction)
- [Historic Deerfield Village ](https://expedia.com/Historic-Deerfield-Village-Deerfield.d553248621532666737.Vacation-Attraction)
- [Eaglebrook School ](https://expedia.com/Eaglebrook-School-Deerfield.d553248635975607512.Vacation-Attraction)
- [Emily Dickinson Museum ](https://expedia.com/Emily-Dickinson-Museum-East-Village-Historic-District.d6091821.Vacation-Attraction)
- [Historic Northampton ](https://expedia.com/Historic-Northampton-Northampton.d553248621532666662.Vacation-Attraction)
- [Eric Carle Museum of Picture Book Art ](https://expedia.com/Eric-Carle-Museum-Of-Picture-Book-Art-Amherst.d6127107.Vacation-Attraction)
- [Smith College Botanic Garden ](https://expedia.com/Smith-College-Botanic-Garden-Northampton.d6070309.Vacation-Attraction)
- [Berkshire Museum ](https://expedia.com/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction)
- [Deerfield Academy ](https://expedia.com/Deerfield-Academy-Deerfield.d553248635974587712.Vacation-Attraction)
- [Mullins Center ](https://expedia.com/Mullins-Center-Amherst.d6213813.Vacation-Attraction)
- [Bridge of Flowers ](https://expedia.com/Bridge-Of-Flowers-Shelburne-Falls.d553248621532666724.Vacation-Attraction)
- [Olympia Ice Center ](https://expedia.com/Olympia-Ice-Center-West-Springfield.d651739847594532864.Vacation-Attraction)
- [Deerfield River ](https://expedia.com/Deerfield-River-United-States-of-America.d682156682122641408.Vacation-Attraction)
- [Mount Greylock State Reservation Visitor Center ](https://expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction)

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