Hotels in Chesterfield

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Feb 17 - Feb 18
Tomorrow
Feb 18 - Feb 19
This weekend
Feb 20 - Feb 22
Next weekend
Feb 27 - Mar 1

Where to stay in Chesterfield?

Front of property
The One Cat B&B
The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78 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 $150
$165 total
includes taxes & fees
Feb 22 - Feb 23
The One Cat B&B
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Windmill Motel Restaurant
Windmill Motel Restaurant
Bernardston
The price is $85
$95 total
includes taxes & fees
Feb 19 - Feb 20
Windmill Motel Restaurant
Front of property
Vikings Villages Resort
Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (166 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 $132
$155 total
includes taxes & fees
Feb 22 - Feb 23
Vikings Villages Resort
Room 4 | Hypo-allergenic bedding, free WiFi, bed sheets
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (346 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
Feb 19 - Feb 20
Colonel Williams Inn
Free daily continental breakfast
The Carriage Barn Inn
The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (168 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 $153
$166 total
includes taxes & fees
Feb 19 - Feb 20
The Carriage Barn Inn
Land view from property
Four Columns Inn
Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (21 reviews)
Escape to this cozy Newfane inn offering free breakfast, WiFi, and parking. The garden-view tavern serves delicious dinner, while nearby attractions like Moore Free Library and Rock River Preserve await exploration.
The price is $129
$141 total
includes taxes & fees
Feb 24 - Feb 25
Four Columns Inn
Exterior
The Inn At Crumpin Fox
The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (353 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 $130
$146 total
includes taxes & fees
Mar 4 - Mar 5
The Inn At Crumpin Fox
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 $111
$121 total
includes taxes & fees
Feb 19 - Feb 20
Best Western Plus Keene Hotel
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, (1,000 reviews)
The price is $81
$88 total
includes taxes & fees
Feb 20 - Feb 21
Days Inn by Wyndham Keene NH
Breakfast area
The Covered Bridge Inn
The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,008 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 $71
$78 total
includes taxes & fees
Feb 19 - Feb 20
The Covered Bridge Inn
Porch
Harvest Barn Inn
Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (250 reviews)
The price is $169
$184 total
includes taxes & fees
Mar 3 - Mar 4
Harvest Barn Inn
Lobby sitting area
Inn at Valley Farms
Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (14 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 $162
$176 total
includes taxes & fees
Feb 19 - Feb 20
Inn at Valley Farms
Exterior
The Burrell House
The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (157 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 $151
$168 total
includes taxes & fees
Feb 20 - Feb 21
The Burrell House
Standard Room, 2 Queen Beds, Refrigerator & Microwave | Desk, iron/ironing board, rollaway beds, free WiFi
The Putney Inn
The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,000 reviews)
The price is $84
$93 total
includes taxes & fees
Mar 8 - Mar 9
The Putney Inn
Exterior
The Inn At Quail Run
The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71 reviews)
The price is $225
$248 total
includes taxes & fees
Feb 19 - Feb 20
The Inn At Quail Run
Lobby
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, (985 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 $104
$113 total
includes taxes & fees
Feb 19 - Feb 20
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (943 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 $114
$125 total
includes taxes & fees
Mar 1 - Mar 2
Hampton Inn Brattleboro
Exterior
Inn on Putney Road
Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
Overlooking the West River, this charming B&B offers lush gardens and a cozy bar/lounge. Just a 15-minute walk from Brattleboro Station and near local attractions. Enjoy free breakfast, WiFi, and parking, plus relaxing deep-tissue massages.
The price is $235
$258 total
includes taxes & fees
Mar 4 - Mar 5
Inn on Putney Road
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, (1,000 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 $139
$153 total
includes taxes & fees
Feb 23 - Feb 24
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Exterior
The Engel House
The Engel House
3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17 reviews)
This inviting B&B offers free breakfast, WiFi, and parking just minutes from Jacksonville Pond and Honora Winery. Outdoor enthusiasts can enjoy nearby hiking trails, kayaking, and mountain biking for an authentic Vermont adventure.
The price is $205
$224 total
includes taxes & fees
Feb 22 - Feb 23
The Engel House
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

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.
See properties

Chesterfield Town Hall

Chesterfield Town Hall is worth a visit when in central Chesterfield.
See properties

Learn more about Chesterfield

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

See all hotels in Chesterfield
Chesterfield showing autumn leaves, building ruins and forests

Check out reviews of Chesterfield hotels guests love

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Very clean room and friendly staff "
Howard 2-night trip
Posted 2 days ago
Courtyard by Marriott Keene Downtown

Frequently asked questions

What accommodations do travelers like in Chesterfield?
Guests like Hampton Inn Brattleboro, Comfort Inn & Suites Brattleboro I-91 and Days Inn by Wyndham Keene NH.
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.