A rural landscape with a grassy field, a dirt path, and a hill covered with autumn-colored trees.

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Our top choices for Chesterfield hotels

A dock extending into a lake with a grassy area in the foreground and trees in the background.
A living room with a sofa, armchair, and round table, a bedroom with a bed and nightstands, and large windows with curtains.
A spacious bedroom with a large bed, a desk, and a television.
A spacious living room with a large window, a patterned rug, and multiple seating options including a sofa and armchairs.

1. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Jason
CA $217
CA $235 total
includes taxes & fees
Nov 1 - Nov 2
Riverside Hotel, an Ascend Collection Hotel
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A lobby with wooden paneling, a fireplace, and two green armchairs.
A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.
A spacious lobby with a stone wall, a reception desk, and a large window.

2. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Francesca
CA $168
CA $185 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Brattleboro
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

3. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
CA $159
CA $175 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Brattleboro I-91
A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.
A two-story white house with a front porch and a garage, surrounded by lush greenery.
A hotel room with two beds, a desk, and a TV.
A grassy field with a playground and trees in the background.

4. The Putney Inn

The Putney Inn
Putney
United States
Elizabeth G
CA $120
CA $132 total
includes taxes & fees
Oct 25 - Oct 26
The Putney Inn
A dining area with a table and four chairs, a painting of a covered bridge, and a painting of a red building.
A reception area with a stone counter, wooden reception desk, and a red carpet.
A multi-story motel with a parking lot, several vehicles parked, and a tree in the foreground.
A hotel room with two beds, a nightstand, a lamp, a painting of a cabin, and a door.

5. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
Adolfo
CA $178
CA $196 total
includes taxes & fees
Oct 6 - Oct 7
The Covered Bridge Inn
A hotel with a clock tower, a parking lot, and a well-maintained garden.
A cozy reading area with wooden chairs, a table with newspapers, and potted plants.
A swimming pool with lounge chairs and a covered umbrella.
A hotel room with a bed, two bedside lamps, a nightstand, a chair, and a small table.

6. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
David
CA $183
CA $201 total
includes taxes & fees
Nov 3 - Nov 4
Black Mountain Inn
The exterior of Latchis Hotel with a prominent entrance, large windows, and potted plants.
A lobby with a central circular platform, a statue, and a fountain. There are paintings on the walls and a staircase to the left.
A hotel lobby with a reception desk, seating area, and a large window.
A banquet hall with round tables, chairs, and a staircase.

7. Latchis Hotel

Latchis Hotel
Brattleboro
United States
jeffrey
CA $253
CA $279 total
includes taxes & fees
Oct 5 - Oct 6
Latchis Hotel
A wooden table set with plates, cutlery, and a folded napkin.
A corner room with wooden flooring, a wooden table, and four chairs. Large windows with curtains are visible, offering a view of a green landscape and a red deck outside.
A two-story building with a porch, a sign indicating guest rooms, and an American flag.
A cozy room with a wooden floor, a rocking chair, a blue armchair, a bookshelf, and a globe on a table.

8. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
CA $194
CA $211 total
includes taxes & fees
Oct 13 - Oct 14
The Carriage Barn Inn
A cozy living room with a fireplace, a coffee station, and a view of the outside.
A motel with multiple floors, each with balconies and windows.
A dining table with a vase of flowers, a chair, and a window with a view.
A hotel room with a sofa, a coffee table, a desk with a telephone, a mirror, and a television.

9. Colonial Motel

Colonial Motel
Brattleboro
Canada
David
CA $118
CA $130 total
includes taxes & fees
Nov 1 - Nov 2
Colonial Motel
A historic brick building with a porch and a sign reading "Burrell House."
A hallway with a white radiator, a wooden staircase, and a door with decorative glass panels.
A kitchen with a microwave, coffee maker, and a KUPPST refrigerator. There are two stools and a small shelf with a vase.
A covered outdoor seating area with tables and chairs, overlooking a residential street with houses and a road.

10. The Burrell House

The Burrell House
Keene
United States
Justin
CA $195
CA $217 total
includes taxes & fees
Oct 22 - Oct 23
The Burrell House
A large, two-story house with a snow-covered driveway and surrounding trees.
A bedroom with a large bed, a blue armchair, a wooden desk, and a view through a glass door.
A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.
A cozy living room with a fireplace, leather chairs, a sofa, and a table with wine glasses.

11. Chesterfield Inn

Chesterfield Inn
West Chesterfield
United States
Wayne
CA $428
CA $465 total
includes taxes & fees
Oct 18 - Oct 19
Chesterfield Inn
A reception area with a counter, a computer, and various informational posters on the wall.
A motel with a central staircase, multiple rooms, and a parking lot.
A reception desk with a computer, a clock, and a refrigerator.
A hotel room with a bed, bedside table, lamp, and a mirror.

12. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
Brattleboro
United States
Donna
CA $90
CA $99 total
includes taxes & fees
Oct 5 - Oct 6
Travelodge by Wyndham Brattleboro VT
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.
A modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.

13. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Angelo
CA $170
CA $184 total
includes taxes & fees
Nov 2 - Nov 3
Keene Elm City Hotel, an Ascend Collection Hotel
A large white building with a stone wall and a lawn covered in fallen leaves.
A room with two single beds, a desk, and a radiator.
A long banquet table set up in a rustic barn with string lights and paper lanterns.
A large white house with a dark roof, surrounded by snow-covered ground and trees.

14. Colonel Williams Inn

Colonel Williams Inn
Brattleboro
United States
Amy
CA $197
CA $217 total
includes taxes & fees
Nov 3 - Nov 4
Colonel Williams Inn
A hotel room with two beds, a TV, a desk, and a window with curtains.
A reception area with a black marble counter, wooden cabinets, and a 'Staff Only' door.
A Days Inn with a brick facade, a central entrance, and a parking lot.
A hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.

15. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
CA $129
CA $140 total
includes taxes & fees
Oct 27 - Oct 28
Days Inn by Wyndham Keene NH
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A covered outdoor area with a wooden deck, white railings, and string lights.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

16. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
CA $198
CA $215 total
includes taxes & fees
Oct 25 - Oct 26
Best Western Plus Keene Hotel
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.
A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.
A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.

17. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Rebecca
CA $199
CA $216 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Keene
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
A hotel lobby with a red carpet, a reception desk, a sofa, and chairs.
A hotel room with two beds, a nightstand, a lamp, and a chair.
A sunroom with large windows, a dining area with a table and chairs, and a sofa.

18. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
United States
David
CA $141
CA $156 total
includes taxes & fees
Nov 3 - Nov 4
Econo Lodge Brattleboro South
A two-story house with a red door, green shutters, and a snow-covered front yard.
A hotel room with a bed, a chair, a desk, a radiator, and a window with curtains.
A golf course with a brick pathway, wooden boxes, and a tee box.
A red building with white trim, surrounded by lush greenery and fruit trees.

19. Centennial House

Centennial House
Northfield
United Kingdom
Alan
CA $235
CA $248 total
includes taxes & fees
Oct 18 - Oct 19
Centennial House
A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.
A wooden interior with a fireplace, a staircase, and a dining area.
A cozy room with a wooden wall, a red sofa, a small table with a bottle, a book, and a plant.
A rustic wooden cabin with a thatched roof, a stone wall, and a wooden staircase leading to a balcony.

20. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Cecil
CA $245
CA $286 total
includes taxes & fees
Oct 13 - Oct 14
Vikings Villages Resort
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Stay near popular Chesterfield attractions

Asbury United Methodist Church

You can learn about the history of Chesterfield with a trip to 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
A stone archway surrounded by lush greenery and trees.
Photo by Shannon Willitts

Top Chesterfield Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"We stay here 2 or 3 times a year and know it well. The staff are always welcoming and helpful. On this visit, we found our original room to be noisy because of the ice machine (?), but the staff got us another room when asked. The room was spacious, quiet and comfortable. The hotel was unusually full, but very quiet. Breakfast is always good here and the coffee is excellent. (Vermont seems to be obsessed with coffee....) Having tried two or three other hotels in Brattleboro, we have settled on the Hampton Inn as our "go to" spot."
Thomas 1-night trip
Posted less than an hour ago
Hampton Inn Brattleboro
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"The staff was friendly and helpful when something was needed. Obviously every hotel has an odor and people who don’t follow rules so yes it smelled of smoke at times. But the sheets smelled fresh and the room was clean. Overall a good quiet stay"
Amanda 5-night trip
Posted 6 hours ago
Days Inn by Wyndham Keene NH
The Covered Bridge Inn

The Covered Bridge Inn

10/10 Excellent
"Good place"
Adolfo 2-night trip
Posted 10 hours ago
The Covered Bridge Inn
Black Mountain Inn

Black Mountain Inn

10/10 Excellent
"Stayed here numerous times."
Charles 1-night trip
Posted 14 hours ago
Black Mountain Inn
Colonial Motel

Colonial Motel

8/10 Good
"I love these kinds of motor lodges and I want them to keep improving and to succeed."
David 1-night trip
Posted 1 day ago
Colonial Motel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Very nice staff and enjoyed my stay."
Charlene 1-night trip
Posted 1 day ago
Comfort Inn & Suites Brattleboro I-91
Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Nice place."
Nicolas 2-night trip
Posted 1 day ago
Vikings Villages Resort
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Bed was more comfortable than most, shower was great and breakfast was good"
Angelo 1-night trip
Posted 2 days ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Putney Inn

The Putney Inn

10/10 Excellent
"Just needed the basics. Putney Inn delivered!"
Gregory 1-night trip
Posted 2 days ago
The Putney Inn

More cheap stays in Chesterfield

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
CA $120
CA $132 total
Oct 25 - Oct 26
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
The Putney Inn
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
CA $129
CA $140 total
Oct 27 - Oct 28
includes taxes & fees
7/10 Good! (1,002 reviews)
Days Inn by Wyndham Keene NH
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
CA $159
CA $175 total
Nov 1 - Nov 2
includes taxes & fees
Comfort Inn & Suites Brattleboro I-91
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
CA $170
CA $184 total
Nov 2 - Nov 3
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
CA $168
CA $185 total
Nov 1 - Nov 2
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
CA $253
CA $279 total
Oct 5 - Oct 6
includes taxes & fees
8.6/10 Excellent! (996 reviews)
Latchis Hotel

Hotels in Chesterfield with star rating

Frequently asked questions

What is the best area to stay in Chesterfield?
The best area to stay in Chesterfield is near Spofford Lake, particularly along the eastern and southern shores, which offer a delightful mix of natural beauty and convenient access to local amenities.This area is centred around the largest lake in Chesterfield, providing a tranquil environment with opportunities for water-based activities. You'll find a selection of accommodations, from charming inns to holiday rentals, many offering lake views or direct access to the water. The main road, Route 9A, runs along the southern edge, making it easy to get around.Couples looking for a peaceful escape will find the lakeside setting particularly appealing. You can enjoy strolls along the shore, leisurely boat trips, or simply relax with views of the water. The quiet atmosphere and natural surroundings are superb for a romantic getaway.Families will also appreciate staying near Spofford Lake. Many properties offer space for children to play, and the lake itself provides activities like swimming and kayaking.
When is the best time to go to Chesterfield?
The best times to visit Chesterfield are during the summer months from June to August and in the autumn from September to October.Summer offers warm weather, superb for enjoying the outdoors. Activities like swimming, boating, and hiking are popular around Spofford Lake. This season is great for families looking for a relaxed getaway with plenty of opportunities for water sports and exploring nature.Autumn transforms Chesterfield with stunning foliage. The rolling hills surrounding the town become a canvas of red, orange, and gold, making it an ideal time for scenic drives and photography.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chesterfield.
How much is the nightly rate at a Chesterfield hotel?
Prices for hotels in Chesterfield often vary, but you can find a great deal from CA $99 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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