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May 2 - May 3
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Top 10 Chesterfield hotels and places to stay

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Interior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 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 3.5 Acres
Interior
Historic Home w/ Modern Updates on 3.5 Acres
3.5 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on 3.5 Acres
The Carriage Barn Inn
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (120)
"The hosts were wonderfully helpful!"
The price is ฿5,415
per night
6 May - 7 May
The Carriage Barn Inn
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The One Cat B&B
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (65)
"This is an awesome B&B! Pat and Conrad are great hosts and they live on site so they are available if you need anything. The room was clean and very spacious. There was comfortable seating in addition to the bed. The room had it's own Keurig machine and it's own AC/heat system. Breakfast the next morning was delicious. Several food and drink options to consider. Also, Conrad bakes his own bread. I had the maple oat bread which was so good. This was my first time in Brattleboro. I will definitely...
The price is ฿6,368
per night
13 May - 14 May
The One Cat B&B
Centennial House
Exterior detail
Centennial House
3.5 star property
9.4 out of 10, Exceptional, (125)
"Loved our stay"
The price is ฿7,356
per night
7 May - 8 May
Centennial House
The Inn At Crumpin Fox
Terrace/patio
The Inn At Crumpin Fox
2.5 star property
9.2 out of 10, Wonderful, (220)
"It was as described"
The price is ฿6,288
per night
16 May - 17 May
The Inn At Crumpin Fox
Hampton Inn & Suites Keene
Reception
Hampton Inn & Suites Keene
2.5 star property
9.0 out of 10, Wonderful, (160)
"The room was comfortable and clean. Breakfast was great "
The price is ฿4,682
per night
26 May - 27 May
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, (895)
"Cleanest hotel bathroom I've ever seen. Good food. Friendly staff. "
The price is ฿4,695
per night
20 May - 21 May
Courtyard by Marriott Keene Downtown
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, (718)
"Great stay, great staff! "
The price is ฿4,686
per night
14 May - 15 May
Holiday Inn Express Keene, an IHG Hotel
Latchis Hotel
Interior
Latchis Hotel
2.5 star property
8.4 out of 10, Very good, (559)
"Fun place to stay "
The price is ฿4,066
per night
5 May - 6 May
Latchis Hotel
Best Western Plus Keene Hotel
Interior entrance
Best Western Plus Keene Hotel
3.0 star property
8.2 out of 10, Very good, (1000)
"breakfast area was the best equipped of any I have ever stayed at!"
The price is ฿5,138
per night
5 May - 6 May
Best Western Plus Keene 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
7.4 out of 10, Good, (870)
"Had a nice stay. Nice and quiet, bed was comfortable and shower had great pressure. The furniture was outdated, but everything was clean and functioned well. Near stores and restaurants and the main roads. The breakfast was a bit lacking, but the coffee was good. "
The price is ฿3,142
per night
9 May - 10 May
Days Inn by Wyndham Keene NH
Econo Lodge Brattleboro
View from room
Econo Lodge Brattleboro
2.0 star property
5.8 out of 10, (485)
"Clean quiet and affordable place with a friendly staff. Small critique: put a small shelf in the shower for shampoo/soap etc. "
The price is ฿4,192
per night
5 May - 6 May
Econo Lodge Brattleboro
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See all available properties in Chesterfield
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.

More cheap stays in Chesterfield

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is ฿3,360 per night from May 15 to May 16
฿3,360
per night
15 May - 16 May
8.2/10 Very Good! (1,006 reviews)

Chesterfield hotels information

Number of reviews
4,684
Accommodation
475 hotels
Lowest Price
฿3,142
Highest Price
฿7,356

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 Colonial Motel And Spa and Hampton Inn Brattleboro. 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 475 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.

Chesterfield Hotel Reviews
Expedia verified reviews

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

5/5 Excellent
Decent overnight stay
"Hotel is no frills but bed and pillows were comfortable, air conditioning worked great, it was clean and the breakfast staff were kind and pleasant. Breakfast was much better than I expected—fresh whole fruit, several flavors of local coffee, hot items, make your own waffle and Greek yogurt for me. "
A verified traveller stayed at Comfort Inn & Suites Brattleboro I-91
Posted 4 days ago
Comfort Inn & Suites Brattleboro I-91
The Putney Inn

The Putney Inn

5/5 Excellent
"Great value "
A verified traveller stayed at The Putney Inn
Posted 3 weeks ago
The Putney Inn