Chesterfield hotels from RM374

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chesterfield hotels

Lobby
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1001)
Experience Vermont comfort at this hotel offering a refreshing indoor pool and 24-hour fitness centre. Located near Brattleboro Bowl with easy access to the train station. Guests love the complimentary breakfast, helpful staff, free WiFi, and convenient parking.
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
The price is RM588
RM647 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (740)
Located minutes from Brattleboro Station, this welcoming hotel offers free breakfast, WiFi, and parking. Work out in the fitness centre before dining at the on-site restaurant. United States Navy Seabee Bridge and Brattleboro Bowl are nearby.
"Price, clean and spacious room, comfy bed."
United States
June
The price is RM457
RM503 total
includes taxes & fees
21 Dec - 22 Dec
Comfort Inn & Suites Brattleboro I-91
Lobby
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (963)
Escape to this quiet retreat with an indoor pool and fitness centre near Ashuelot River. Just minutes from local shops and eateries, this hotel offers free breakfast, WiFi, and parking. The helpful staff ensures a comfortable stay for business or leisure travellers.
"The room was perfect, and the food was great "
United States
Paul
The price is RM482
RM523 total
includes taxes & fees
21 Dec - 22 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (926)
Located minutes from Brattleboro Station, this welcoming hotel offers a relaxing hot tub and fitness centre for unwinding after exploring. Enjoy the complimentary breakfast before visiting nearby United States Navy Seabee Bridge or grabbing coffee at the café.
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is RM600
RM660 total
includes taxes & fees
25 Dec - 26 Dec
Hampton Inn Brattleboro
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1003)
"Nice motel. "
United States
Richard
The Putney Inn
Sun deck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (629)
This classic New Hampshire hotel offers a 24-hour fitness centre and free WiFi. Located near United States Navy Seabee Bridge, guests can enjoy cross-country skiing and snowboarding. Clean rooms, helpful staff, and complimentary parking enhance your countryside retreat.
"Clean room, beautiful location"
United States
Marcie
The price is RM622
RM674 total
includes taxes & fees
15 Jan - 16 Jan 2026
Riverside Hotel, an Ascend Collection Hotel
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
The price is RM737
RM799 total
includes taxes & fees
5 Jan - 6 Jan 2026
Fairfield Inn & Suites by Marriott Keene Downtown
Dining
Farm Road Estate

Farm Road Estate

Farm Road Estate
3.0 star property
West Dover
10.0 out of 10, Exceptional, (77)
Set in West Dover, this golf hotel offers both winter and summer fun with a seasonal outdoor pool and restaurant. Just a short drive to Mount Snow and its golf course, guests can unwind with massages or drinks at the bar after an adventurous day outdoors.
"Room was clean, staff friendly, amenities were good"
United States
Movses
Farm Road Estate
Restaurant
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1002)
This hotel offers quiet rooms and a peaceful environment near the Ashuelot River. Enjoy complimentary breakfast, WiFi, and parking. Guests love the helpful staff and convenient location. Visit the 24-hour fitness centre or unwind with a drink at the bar after exploring nearby attractions.
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is RM528
RM573 total
includes taxes & fees
21 Dec - 22 Dec
Best Western Plus Keene Hotel
Front of property
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (474)
Wake up to a peaceful mountain retreat where hiking and biking adventures await just outside. After exploring local trails, cool off in the seasonal pool. Free breakfast, WiFi and parking enhance this quiet Brattleboro haven.
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is RM418
RM460 total
includes taxes & fees
22 Dec - 23 Dec
Black Mountain Inn
Restaurant
The White House Inn

The White House Inn

The White House Inn
3.5 star property
Wilmington
9.2 out of 10, Wonderful, (262)
Enjoy a charming Vermont getaway with on-site dining and a welcoming bar/lounge. Located near South Main Street and Pettee Memorial Library, this hotel offers free WiFi, complimentary parking, and peaceful garden views. Helpful staff ensure a pleasant stay.
"The room was beautiful and the historic charm was wonderful "
United States
Karin
The price is RM678
RM746 total
includes taxes & fees
7 Jan - 8 Jan 2026
The White House Inn
Free daily buffet breakfast
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (353)
Free breakfast, parking, and 24-hour fitness centre make this Keene hotel a great choice. Swim in the indoor pool or request room service after exploring nearby Cheshire Children's Museum. Travellers praise the helpful staff and morning meal.
"Clean comfy nice staff "
United States
Katherine
The price is RM674
RM731 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Keene
Front of property
Colonel Williams Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
Enjoy a cosy stay at this Brattleboro inn with complimentary local cuisine breakfast and WiFi. Outdoor enthusiasts can explore nearby cross-country and downhill skiing options. A garden, terrace, and helpful staff enhance the peaceful Vermont experience.
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is RM643
RM708 total
includes taxes & fees
18 Dec - 19 Dec
Colonel Williams Inn
Breakfast area
The Covered Bridge Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
Set in Brattleboro, this charming inn sits near hiking trails and winter sports activities. Enjoy free continental breakfast each morning, complimentary WiFi, and parking. The United States Navy Seabee Bridge and Brattleboro Bowl are just minutes away.
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is RM368
RM405 total
includes taxes & fees
18 Dec - 19 Dec
The Covered Bridge Inn
Exterior
Colonial Motel And Spa

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1001)
Located in Brattleboro, this motel offers American cuisine at India Masala House restaurant and a welcoming bar. Comfortable rooms include refrigerators and microwaves, while the spa provides relaxing massage treatments near Brattleboro Bowl.
"Nice place to stay for the night."
United States
Robin
The price is RM471
RM518 total
includes taxes & fees
18 Dec - 19 Dec
Colonial Motel And Spa
Exterior
Latchis Hotel

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very good, (837)
"Great stay"
United States
Jason
The price is RM497
RM547 total
includes taxes & fees
18 Dec - 19 Dec
Latchis Hotel
Porch
Harvest Barn Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Pub
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1003)
Stylish accommodation in Keene City centre, close to Colonial Theatre and Central Square. Enjoy a refreshing swim in the indoor pool, grab a bite at the coffee shop, then unwind at the bar. Free WiFi and parking make exploring the area convenient.
"Very comfortable and clean."
United States
Christina
The price is RM735
RM798 total
includes taxes & fees
24 Dec - 25 Dec
Courtyard by Marriott Keene Downtown
Exterior
The Burrell House

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
Walking distance to Central Square, this inviting guesthouse offers complimentary WiFi and self parking. Enjoy the outdoor picnic area after exploring nearby attractions like CC&H Framing and Pepper Pete's Hot Shop.
"Very helpful, kind staff"
United States
Paitris
The Burrell House
Exterior
The Inn At Quail Run

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is RM716
RM788 total
includes taxes & fees
23 Dec - 24 Dec
The Inn At Quail Run
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Chesterfield attractions

Asbury United Methodist Church

You can learn about the history of Chesterfield when you stop by Asbury United Methodist Church. Amble around the area's riverfront or seek out its ski slopes.
See properties

Chesterfield Town Hall

After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Make some time to visit the shops while you're in the area.
See properties

Learn more about Chesterfield

Tucked along the Connecticut River, this charming New England town offers peaceful kayaking and hiking trails through Pisgah State Park. Spend summer days swimming at Spofford Lake, where local families gather for picnics and the annual Old Home Day celebrations.

See all hotels in Chesterfield
Chesterfield featuring fall colors, forests and building ruins

Top Chesterfield Hotel Reviews

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Room clean and comfortable "
Letitia 1-night trip
Posted 5 days ago
Latchis Hotel

More cheap stays in Chesterfield

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is RM344 per night from 23 Dec to 24 Dec
RM344
RM374 total
23 Dec - 24 Dec
includes taxes & fees
7/10 Good! (999 reviews)

Frequently asked questions

Where is the best place to stay in Chesterfield?
The Covered Bridge Inn, located 4.4 mi (7.1 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 Comfort Inn & Suites Brattleboro I-91. 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 is staying in Chesterfield like?
Visitors can enjoy all that Chesterfield has to offer, including the shopping and restaurants. There are 520 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 Sherris Castle Ruins 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.

Explore a world of travel with Expedia