Chesterfield Hotels from S$109

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Chesterfield hotel prices

Tonight
26 Nov - 27 Nov
Tomorrow night
27 Nov - 28 Nov
This weekend
29 Nov - 1 Dec
Next weekend
6 Dec - 8 Dec

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Chesterfield hotels

Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (678)
"Took Amtrak and decided to spend one night in town. Hotel conveniently located to station, local bus, and shops/restaurants. Easily walkable to anywhere you need to go, and movie theater next door had convenient timings. Clean room, comfortable bed, and so much space in the room. "
The price is S$180
includes taxes & fees
4 Dec - 5 Dec
Latchis Hotel
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (963)
"Great rooms and service love it my favorite place to stay in Keene "
The price is S$114
includes taxes & fees
19 Dec - 20 Dec
Days Inn by Wyndham Keene NH
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (256)
"We had an issue with the TV in our assigned room, the staff was quick to rectify the problem. Friendly staff. This is our 3rd time staying there, and will go back"
The price is S$197
includes taxes & fees
2 Dec - 3 Dec
Hampton Inn & Suites Keene
Courtyard by Marriott Keene Downtown
Hypo-allergenic bedding, in-room safe, desk, laptop workspace

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (994)
"Well appointments room, very spacious and quiet. Fan I bathroom did not work "
The price is S$154
includes taxes & fees
1 Dec - 2 Dec
Courtyard by Marriott Keene Downtown
Best Western Plus Keene Hotel
Exterior

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1061)
"Best breakfast. Balcony is too small you can’t even put a chair on it"
The price is S$193
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Keene Hotel
Holiday Inn Express Keene, an IHG Hotel
Indoor pool

Holiday Inn Express Keene, an IHG Hotel

2.5 star property
8.4 out of 10, Very good, (799)
"Nice clean room comfortable I would stay again when in the area. "
The price is S$152
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Express Keene, an IHG Hotel
Econo Lodge Brattleboro
View from room

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (515)
"It was fine. We just stopped in for the night after a concert"
The price is S$120
includes taxes & fees
4 Dec - 5 Dec
Econo Lodge Brattleboro
The Inn At Crumpin Fox
Terrace/patio

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (274)
"Near good dining…."
The price is S$314
includes taxes & fees
4 Dec - 5 Dec
The Inn At Crumpin Fox
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (142)
"Lovely old BnB, easy to find, very convenient Very clean room Great continental breakfast Loved ease of walking to downtown, many stores and restaurants Informative and very friendly and helpful owner"
The price is S$267
includes taxes & fees
5 Dec - 6 Dec
The Carriage Barn Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (145)
"Lovely bed & breakfast!!! We appreciate the hospitality and delicious breakfast. "
The price is S$255
includes taxes & fees
30 Nov - 1 Dec
Centennial House
The One Cat B&B
Exterior detail

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (74)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The One Cat B&B
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Property grounds

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2.5 star property
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Private kitchen

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, laptop workspace, iron/ironing board, bed sheets

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
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.
Don't see what you're looking for?
See all available properties in Chesterfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

Where is the best place to stay in Chesterfield?

Colonial Motel And Spa, located 4.5 mi (7.3 km) from the heart of Chesterfield, is a top choice for your stay, based on our traveller data. Other good options for your stay in the area are Hampton Inn Brattleboro and The Covered Bridge Inn. See all available top hotels, or vacation rentals in Chesterfield.

If I need to cancel my hotel reservation in Chesterfield, will I receive a refund?

Yes! Most hotel room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chesterfield.

What are some accommodation options with pools in Chesterfield?

Colonial Motel And Spa: Features 2 indoor swimming pools, a children's pool and a sauna. Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel and Hampton Inn Brattleboro are a couple of other choices with an on-site pool. View all hotels with pools in Chesterfield.

What is staying in Chesterfield like?

Visitors can enjoy all that Chesterfield has to offer, including the shopping and restaurants. There are 478 hotels and other accommodation options in the surrounding area. Find out more about Chesterfield.

What should I see while I'm in Chesterfield?

A couple of favourite places to visit are Asbury United Methodist Church and Pisgah State Park. You'll also find Spofford Lake and Madame Sherri Forest in the area. Take a look at what more there is to see and do in Expedia's Chesterfield guide.

What's the weather like in Chesterfield?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Chesterfield are January, March, November and February, with each month seeing an average of 23 cm of snowfall.