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Our top choices for Chesterfield hotels

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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, (751)
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.
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is NZ$267
includes taxes & fees
4 Jan - 5 Jan
Comfort Inn & Suites Brattleboro I-91
Indoor pool
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, (971)
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.
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is NZ$242
includes taxes & fees
1 Feb - 2 Feb
Keene Elm City Hotel, an Ascend Collection Hotel
Front of property
The Inn At Crumpin Fox

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (346)
Set in picturesque surroundings, this charming inn offers easy access to nearby hiking and mountain biking trails. Free WiFi and parking enhance your stay while the helpful staff ensures comfort. Just minutes from Cushman Library and Powers Institute Museum.
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
The price is NZ$245
includes taxes & fees
31 Jan - 1 Feb
The Inn At Crumpin Fox
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1000)
"The room was okay for a quick stop to rest. "
United States
Janice
The Putney Inn
Exterior detail
The Covered Bridge Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1000)
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.
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
United States
Megan
The price is NZ$151
includes taxes & fees
2 Jan - 3 Jan
The Covered Bridge Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (166)
This cosy Carriage Barn Inn provides complimentary continental breakfast, WiFi, and parking. Located near Thorne-Sagendorph Art Gallery, the bed and breakfast creates a perfect base for exploring Keene's cultural attractions.
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is NZ$235
includes taxes & fees
4 Jan - 5 Jan
The Carriage Barn Inn
Premium bedding, individually decorated, individually furnished, desk
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, (1001)
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 NZ$279
includes taxes & fees
2 Jan - 3 Jan
Best Western Plus Keene 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
Garden
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (16)
Wake up to free breakfast at this cosy Vermont inn before exploring nearby Rock River Preserve. The on-site Tavern restaurant serves dinner with beautiful garden views, while the welcoming bar and free WiFi create a relaxing countryside retreat.
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Hiking
Latchis Hotel

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very good, (841)
"Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!"
United States
Jaime
The price is NZ$227
includes taxes & fees
4 Jan - 5 Jan
Latchis Hotel
Exterior
The One Cat B&B

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
Charming accommodation just 5 minutes' walk from Brattleboro Station. Enjoy daily full breakfast, free WiFi, and parking. After exploring nearby museums and theatres, return for hiking, kayaking, and mountain biking adventures.
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is NZ$248
includes taxes & fees
6 Jan - 7 Jan
The One Cat B&B
Interior detail
The White House Inn

The White House Inn

The White House Inn
3.5 star property
Wilmington
9.2 out of 10, Wonderful, (269)
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.
"We stayed at the White House in two weekends in a row while our house was under construction. We loved that they had music until 9 and that the room was clean and the beds were comfortable. The staff made sure we had everything we needed. We would definitely recommend."
United States
Stacy
The price is NZ$315
includes taxes & fees
1 Feb - 2 Feb
The White House Inn
Free breakfast
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (930)
Located minutes from Brattleboro Station, this welcoming hotel offers a relaxing spa pool 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.
"Good breakfast, great staff and very good location "
United States
Valdeci
The price is NZ$279
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn Brattleboro
Front of property
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (476)
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.
"Room looked good. Wish they have shampoo. Only one soap. Nice shower pressure. Would visit again "
United States
Miles
The price is NZ$210
includes taxes & fees
12 Jan - 13 Jan
Black Mountain Inn
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 NZ$339
includes taxes & fees
8 Jan - 9 Jan
Fairfield Inn & Suites by Marriott Keene Downtown
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 NZ$287
includes taxes & fees
28 Jan - 29 Jan
Colonel Williams 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, (633)
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 NZ$301
includes taxes & fees
1 Feb - 2 Feb
Riverside Hotel, an Ascend Collection Hotel
Exterior
The Burrell House

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156)
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.
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House
Free daily on-the-go breakfast
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, (1002)
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 NZ$285
includes taxes & fees
4 Jan - 5 Jan
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (362)
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 NZ$312
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn & Suites Keene
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.
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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 autumn colours, building ruins and forests

Top Chesterfield Hotel Reviews

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"Excellent stay at the Riverside. Big clean room with an amazing view. "
Rae 2-night trip
Posted 3 days ago
Riverside Hotel, an Ascend Collection Hotel

More cheap accommodation in Chesterfield

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road Brattleboro VT
The price is NZ$151 per night from 2 Jan to 3 Jan
NZ$151
2 Jan - 3 Jan
includes taxes & fees
7.6/10 Good! (1,002 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 The White House Inn and Comfort Inn & Suites Brattleboro I-91. See all available top hotels, or vacation rentals in Chesterfield.
What are some of the best holiday rentals that Chesterfield has to offer?
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Chesterfield is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. See all 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 521 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, Chesterfield Town Hall 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.

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