Chesterfield Hotels from S$108

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
12 Jul - 13 Jul
Tomorrow
13 Jul - 14 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Chesterfield hotels

The Inn At Crumpin Fox
Welcome to The Inn at Crumpin-Fox, set amidst a beautiful landscaped area with vibrant tulips.

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (302)
"Very nice and very responsive staff"
The price is S$271
includes taxes & fees
14 Jul - 15 Jul
The Inn At Crumpin Fox
The Covered Bridge Inn
Experience the charm of The Covered Bridge Inn, nestled in a lush setting with a welcoming atmosphere.

The Covered Bridge Inn

2.5 star property
8.0 out of 10, Very good, (1006)
"Clean, convenient, comfortable and good price. "
The Covered Bridge Inn
Black Mountain Inn
Check the time from the central clock tower and enjoy a convenient entrance with a covered porch.

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (443)
"Courteous, helpful staff Convenient to highways and downtown Comfortable grounds Easy sleeping"
The price is S$169
includes taxes & fees
6 Aug - 7 Aug
Black Mountain Inn
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indulge in a variety of dishes, including cheese omelets and sandwiches, at our buffet.

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (995)
"The nicest Holiday Inn Express I have ever stayed at. Lovely place and super clean."
The price is S$252
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Best Western Plus Keene Hotel
Welcome to Best Western PLUS, featuring a clean and modern exterior with a prominent logo and inviting entrance.

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1000)
"Nice hotel "
The price is S$186
includes taxes & fees
14 Jul - 15 Jul
Best Western Plus Keene Hotel
Colonial Motel And Spa
Colonial Motel features a traditional design with a brick chimney and metal roof.

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1007)
"Great place "
The price is S$138
includes taxes & fees
14 Jul - 15 Jul
Colonial Motel And Spa
Travelodge by Wyndham Brattleboro VT
Welcome to our reception area, where friendly staff are available to assist with your stay. The reception desk offers a computer and telephone for your convenience.

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (683)
"Quiet, comfortable and dog friendly. Pleasant host at check in"
The price is S$100
includes taxes & fees
14 Jul - 15 Jul
Travelodge by Wyndham Brattleboro VT
Comfort Inn & Suites Brattleboro I-91
Relax in our inviting lobby, featuring a seating area with sofas and a reception desk with amenities.

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (650)
"Beds were comfortable and Desk attendant was very nice "
The price is S$195
includes taxes & fees
6 Aug - 7 Aug
Comfort Inn & Suites Brattleboro I-91
Riverside Hotel, Ascend Hotel Collection
Relax on the lakeside dock, surrounded by lush greenery and a tranquil atmosphere.

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (575)
"Great hotel experience from the moment we checked in. The service was excellent, hotel and rooms were so clean, and the sleep number bed was the best! It's a gem of a hotel! "
The price is S$211
includes taxes & fees
14 Jul - 15 Jul
Riverside Hotel, Ascend Hotel Collection
Days Inn by Wyndham Keene NH
Two double beds with blue bedding and a blue accent wall create a cozy atmosphere.

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1004)
"Great stay"
The price is S$126
includes taxes & fees
27 Jul - 28 Jul
Days Inn by Wyndham Keene NH
Fairfield Inn & Suites by Marriott Keene Downtown
Classic architecture meets modern comfort at this inviting hotel entrance.

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (724)
"We had a lovely stay. Decent breakfast, clean facilities. "
The price is S$221
includes taxes & fees
21 Jul - 22 Jul
Fairfield Inn & Suites by Marriott Keene Downtown
Windham Hill Inn
Guests can enjoy a serene view of the surrounding landscape from this outdoor deck.

Windham Hill Inn

4.0 star property
8.4 out of 10, Very good, (36)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
The price is S$264
includes taxes & fees
13 Jul - 14 Jul
Windham Hill Inn
Hampton Inn Brattleboro
Enjoy a casual dining experience with a focus on comfort and convenience in our kitchen area.

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (843)
"Great hotel, friendly staff and very comfortable."
The price is S$178
includes taxes & fees
20 Jul - 21 Jul
Hampton Inn Brattleboro
The Putney Inn
Welcome to The Putney Inn, a restaurant and motel with a warm and inviting sign.

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1000)
"Quaint little Inn with spacious rooms and comfy beds. Just perfect and the guy at the front desk was super friendly and helpful! Would stay again if in the area "
The Putney Inn
Deerfield Valley Inn
Surrounded by snow-covered trees, this serene winter scene offers a peaceful retreat.

Deerfield Valley Inn

3.0 star property
9.4 out of 10, Exceptional, (51)
"Overall great spot!"
Deerfield Valley Inn
Hampton Inn & Suites Keene
Welcome to the Granite State hotel, featuring a reception area and suite shop.

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (311)
"We had a great time here! Clean rooms, polite staff and nice dinning area"
The price is S$205
includes taxes & fees
20 Jul - 21 Jul
Hampton Inn & Suites Keene
Keene Elm City Hotel, Ascend Hotel Collection
Relax by the pool surrounded by a spacious deck and lounge chairs.

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (854)
"Friendly staff and clean, spacious room. Breakfast was very good!! "
The price is S$155
includes taxes & fees
21 Jul - 22 Jul
Keene Elm City Hotel, Ascend Hotel Collection
Centennial House
Enjoy meals in a beautifully lit dining area with arched windows and a view of the outdoors.

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (154)
"This historic property is very nice. Beds are comfortable. The hosts are very welcoming and communication was very good. Breakfast was outstanding! I highly recommend this property and hope to return for another visit someday. "
The price is S$235
includes taxes & fees
16 Jul - 17 Jul
Centennial House
The Carriage Barn Inn
Enjoy a meal with a view from this dining table near a window.

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (152)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is S$246
includes taxes & fees
13 Jul - 14 Jul
The Carriage Barn Inn
Inn on Putney Road
Classic two-story house with a gabled roof and symmetrical facade, surrounded by a well-maintained garden and a white fence.

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (48)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is S$373
includes taxes & fees
20 Jul - 21 Jul
Inn on Putney Road
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Chesterfield

Escape to Chesterfield! Enjoy its dining and history.

See all hotels in Chesterfield
Chesterfield which includes tranquil scenes, autumn leaves and forests

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 Latchis Hotel. 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 510 hotels and other accommodation options in the surrounding area. Find out more about Chesterfield.

What should I see while I'm in Chesterfield?

Favourite places to visit include Asbury United Methodist Church, Pisgah State Park and Chesterfield Town Hall. 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.