Hotels in Chesterfield

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Check prices for these dates

This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

Where to stay in Chesterfield?

Deluxe Double Room, 1 Queen Bed, Valley View | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
8.8 out of 10, Excellent, (22 reviews)
The price is $135
$151 total
includes taxes & fees
Jul 2 - Jul 3
Windmill Motel Restaurant
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
Surrounded by winter adventures, this charming B&B offers free local cuisine breakfast, WiFi, and parking. Nearby Southern Vermont Natural History Museum and Hogback Mountain Conservation Area provide natural escapes, while the helpful staff ensures a memorable stay.
The price is $158
$173 total
includes taxes & fees
Jul 2 - Jul 3
Colonel Williams Inn
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (373 reviews)
Nestled in Bernardston with nearby hiking trails, kayaking, and mountain biking opportunities, this welcoming inn offers free WiFi and parking. Close to Cushman Library and Powers Institute Museum, guests consistently praise the helpful staff and clean rooms.
The price is $162
$181 total
includes taxes & fees
Jul 14 - Jul 15
The Inn At Crumpin Fox
Lobby

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,002 reviews)
Escape to this welcoming hotel in Keene, where you'll find an indoor pool and fitness center near local shops and eateries. Despite its commercial location, guests enjoy a quiet atmosphere, free breakfast, and helpful staff to enhance your stay.
The price is $109
$118 total
includes taxes & fees
Jul 12 - Jul 13
Keene Elm City Hotel, an Ascend Collection Hotel
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
Quiet rooms welcome travelers to this restful retreat near the Ashuelot River and Thorne Sagendorph Art Gallery. The restaurant and bar provide delicious meals, while fellow guests rave about the free breakfast and helpful staff.
The price is $127
$138 total
includes taxes & fees
Jul 2 - Jul 3
Best Western Plus Keene Hotel
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
Tucked into walkable Keene, this cozy guesthouse offers free WiFi and convenient self parking. Explore nearby Central Square and local shops, then unwind in the peaceful picnic area after a day of adventures.
The price is $142
$158 total
includes taxes & fees
Jul 6 - Jul 7
The Burrell House
Lobby

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, (1,001 reviews)
Splash into the indoor pool at this welcoming Brattleboro hotel near United States Navy Seabee Bridge. Free breakfast, WiFi and parking enhance your stay while the 24-hour fitness center keeps routines on track. Guests consistently praise the helpful staff.
The price is $149
$164 total
includes taxes & fees
Jul 2 - Jul 3
Holiday Inn Express Hotel & Suites Brattleboro by IHG
In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,004 reviews)
The price is $88
$96 total
includes taxes & fees
Jul 12 - Jul 13
Days Inn by Wyndham Keene NH
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (1,000 reviews)
Immerse yourself in Brattleboro charm at this welcoming hotel with complimentary breakfast and parking. Unwind in the hot tub, energize at the fitness center, or grab a coffee at the café while exploring nearby attractions like Brattleboro Bowl.
The price is $122
$134 total
includes taxes & fees
Jul 12 - Jul 13
Hampton Inn Brattleboro
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (915 reviews)
The price is $111
$122 total
includes taxes & fees
Jul 5 - Jul 6
Latchis Hotel
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
Wake up to continental breakfast at this cozy Keene B&B, located near the Thorne-Sagendorph Art Gallery. Enjoy free WiFi and parking while exploring the area, with Manchester-Boston Regional Airport and Brattleboro Station both accessible for day trips.
The price is $181
$196 total
includes taxes & fees
Jul 14 - Jul 15
The Carriage Barn Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (80 reviews)
Wake up to a complimentary full breakfast at this cozy cat-themed B&B. Just a 5-minute walk from Brattleboro Station with nearby hiking trails, kayaking, and mountain biking. New England Youth Theatre and Brattleboro Museum & Art Center wait to be explored.
The price is $250
$275 total
includes taxes & fees
Jul 6 - Jul 7
The One Cat B&B
Front of property

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (200 reviews)
Enjoy mountain adventures from this secluded retreat with free WiFi and parking. Kayak, bike, or snowshoe directly from the property. Helpful staff ensure a memorable stay near Shattuck Brook Wildlife Management Area.
The price is $172
$201 total
includes taxes & fees
Jul 26 - Jul 27
Vikings Villages Resort
Exterior

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.2 out of 10, Wonderful, (74 reviews)
The price is $225
$248 total
includes taxes & fees
Jul 2 - Jul 3
The Inn At Quail Run
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (823 reviews)
Warm Brattleboro accommodations with complimentary breakfast, WiFi, and parking just minutes from United States Navy Seabee Bridge. Energize at the fitness center after exploring nearby attractions. Fellow travelers consistently praise the exceptionally helpful staff.
The price is $119
$131 total
includes taxes & fees
Jul 26 - Jul 27
Comfort Inn & Suites Brattleboro I-91
Lobby sitting area

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (19 reviews)
Unwind in this welcoming inn with complimentary WiFi and parking, surrounded by garden scenery. Just minutes from Hooper Golf Course and Club, this countryside retreat offers a perfect base for exploring local attractions near Springfield and Bellows Falls.
The price is $186
$202 total
includes taxes & fees
Jul 2 - Jul 3
Inn at Valley Farms
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (268 reviews)
The price is $174
$190 total
includes taxes & fees
Jul 19 - Jul 20
Harvest Barn Inn
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (783 reviews)
The price is $161
$174 total
includes taxes & fees
Jul 7 - Jul 8
Fairfield Inn & Suites by Marriott Keene Downtown
Free daily continental breakfast

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,002 reviews)
Tucked into scenic Brattleboro, this inn welcomes outdoor enthusiasts with nearby hiking, snowboarding, and sledding options. Start each day with complimentary continental breakfast before exploring local attractions like the Brattleboro Bowl just minutes away.
The price is $128
$140 total
includes taxes & fees
Jul 30 - Jul 31
The Covered Bridge Inn
Sundeck

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (659 reviews)
The price is $152
$165 total
includes taxes & fees
Jul 12 - Jul 13
Riverside Hotel, an Ascend Collection Hotel
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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Top landmarks in Chesterfield

Asbury United Methodist Church

If you're planning a bit of sightseeing during your trip, head to Asbury United Methodist Church— just one of the monuments in central Chesterfield.
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Learn more about Chesterfield

Chesterfield is well-known for its attractions such as Asbury United Methodist Church and Chesterfield Town Hall.

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A stone archway in a forest with autumn leaves.

Check out reviews of Chesterfield hotels guests love

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"I had a wonderful stay! The staff was so helpful and I felt very safe as a solo traveler!"
Cara 3-night trip
Posted less than an hour ago
Riverside Hotel, an Ascend Collection Hotel

Frequently asked questions

What accommodations do travelers like in Chesterfield?
Guests like Latchis Hotel, Best Western Plus Keene Hotel and Hampton Inn Brattleboro.
Can I book refundable hotels in Chesterfield?
If you're looking for the flexibility to change your travel plans to Chesterfield, most properties offer refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.
What will the weather in Chesterfield be like during my visit?
The warmest months in Chesterfield are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 27°F. The rainiest months are October and December.
Why should I book my Chesterfield hotel through Hotels.com?
There are plenty of reasons to book your Chesterfield travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.