A U.S. Post Office in Chesterfield, N.H. with stone walls and green shutters.

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Dates

November 2026

December 2026

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No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterfield

A dock extending into a lake with a grassy area in the foreground and trees in the background.

1. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Steve

$141 nightly

Dec 6 - Dec 7

Total with taxes and fees

A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

2. Hampton Inn Brattleboro

Brattleboro

Faith

$112 nightly

Nov 15 - Nov 16

Total with taxes and fees

A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

3. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

$114 nightly

Nov 22 - Nov 23

Total with taxes and fees

A hotel room with a bed, a desk with a chair, a TV, a mirror, and a wardrobe.

4. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

$139 nightly

Dec 6 - Dec 7

Total with taxes and fees

A hotel with a clock tower, a parking lot, and a well-maintained garden.

5. Black Mountain Inn

Brattleboro

Ron

$103 nightly

Nov 8 - Nov 9

Total with taxes and fees

The exterior of Latchis Hotel with a classic architectural style, large windows, and a prominent entrance.

6. Latchis Hotel

Brattleboro

Erik

$113 nightly

Nov 9 - Nov 10

Total with taxes and fees

A hotel room with two beds, a desk, and a TV.

7. The Putney Inn

Putney

Kristen

$78 nightly

Dec 6 - Dec 7

Total with taxes and fees

A reception area with a counter, a computer, and various informational posters on the wall.

8. Travelodge by Wyndham Brattleboro VT

Brattleboro

Cara

$60 nightly

Nov 8 - Nov 9

Total with taxes and fees

A hotel room with two beds, a nightstand, a lamp, a painting of a cabin, and a door.

9. The Covered Bridge Inn

Brattleboro

Rick

$130 nightly

Dec 5 - Dec 6

Total with taxes and fees

A cozy living room with a fireplace, a coffee station, and a view of the outside.

10. Colonial Motel

Brattleboro

Swaraj

$95 nightly

Nov 8 - Nov 9

Total with taxes and fees

A large, two-story house with a snow-covered driveway and surrounding trees.

11. Chesterfield Inn

West Chesterfield

Wayne

$301 nightly

Nov 8 - Nov 9

Total with taxes and fees

A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

12. Inn on Putney Road

Brattleboro

Karla

$267 nightly

Nov 8 - Nov 9

Total with taxes and fees

A hotel room with two beds, a TV, a desk, and a window with curtains.

13. Days Inn by Wyndham Keene NH

Keene

CHERYL

$97 nightly

Nov 8 - Nov 9

Total with taxes and fees

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

14. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

$134 nightly

Nov 8 - Nov 9

Total with taxes and fees

A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

15. Best Western Plus Keene Hotel

Keene

Ruddy

$135 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

16. Hampton Inn & Suites Keene

Keene

Dayle

$153 nightly

Dec 5 - Dec 6

Total with taxes and fees

A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

17. Econo Lodge Brattleboro South

Brattleboro

Luis

$99 nightly

Dec 6 - Dec 7

Total with taxes and fees

A modern outdoor lounge area with two lounge chairs and a wooden deck.

18. Otherland Hotel

Newfane

Debi

$164 nightly

Nov 8 - Nov 9

Total with taxes and fees

A historic brick building with a porch and a sign reading "Burrell House."

19. The Burrell House

Keene

Carol

$129 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

20. Vikings Villages Resort

Guilford

Cecil

$223 nightly

Nov 8 - Nov 9

Total with taxes and fees

View all 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

Top reviews in Chesterfield

Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

10/10 Excellent

James

Inn on Putney Road

Brattleboro

10/10 Excellent

Victoria

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

10/10 Excellent

Anthony

Chesterfield Inn

West Chesterfield

10/10 Excellent

Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.

Beverly

Comfort Inn & Suites Brattleboro I-91

Brattleboro

10/10 Excellent

Julianne

Hampton Inn Brattleboro

Brattleboro

10/10 Excellent

Arrived late and were greeted by 2 friendly associates at the desk. There were coffee, tea, hot cocoa, cookies, cheese and crackers available. A welcoming lobby with fireplace. Room was nice, comfortable and clean. Lots of outlets in room. Indoor pool was nice, clean, and heated. hot tub was very relaxing after days of skiing. Continental breakfast was very good and had a variety of choices. We were pleasantly surprised with our choice.

K.White

Latchis Hotel

Brattleboro

10/10 Excellent

Anonymous traveler

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A room with two single beds, a desk, and a radiator.

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

A two-story house with a red door, green shutters, and a snow-covered front yard.

Centennial House

Northfield

10/10 Excellent

My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne

Anonymous traveler

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

The Inn At Crumpin Fox

Bernardston

10/10 Excellent

I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.

Anonymous traveler

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A windmill, a row of cabins, and a grassy field at night.

Windmill Motel Restaurant

Bernardston

10/10 Excellent

Marjorie

Hampton Inn & Suites Keene

Keene

10/10 Excellent

kristin

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

10/10 Excellent

Kristine

Frequently Asked Questions

Why book your condo in Chesterfield with Expedia?

Booking a condo in Chesterfield is as easy as working out your travel dates and choosing an option that suits your style. Looking for something budget friendly or upmarket, or a stay that also features a kitchen and laundry? Use Expedia's search filters to further narrow your search results and find the ideal fit.

How can I find cheap condos in Chesterfield?

With Expedia's user-friendly filter tool, booking cheap condos in Chesterfield is a cinch. To find properties that'll make your wallet happy, narrow down your search by amenities, budget and star rating.

What is there to do in Chesterfield near my condo?

If you're ready to explore the sights of Chesterfield, make tracks to Asbury United Methodist Church. It's a winner with visitors and locals alike.

Explore a world of travel with Expedia

Keene Vacation Rentals
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Search and Rent Chesterfield Condos

Bundle & Save

OneKeyCash

Upfront pricing

Find vacation rentals that suit your style

Check prices for these dates

Recommended hotels in Chesterfield

1. Riverside Hotel, an Ascend Collection Hotel

2. Hampton Inn Brattleboro

3. Comfort Inn & Suites Brattleboro I-91

4. Holiday Inn Express Hotel & Suites Brattleboro by IHG

5. Black Mountain Inn

6. Latchis Hotel

7. The Putney Inn

8. Travelodge by Wyndham Brattleboro VT

9. The Covered Bridge Inn

10. Colonial Motel

11. Chesterfield Inn

12. Inn on Putney Road

13. Days Inn by Wyndham Keene NH

14. Keene Elm City Hotel, an Ascend Collection Hotel

15. Best Western Plus Keene Hotel

16. Hampton Inn & Suites Keene

17. Econo Lodge Brattleboro South

18. Otherland Hotel

19. The Burrell House

20. Vikings Villages Resort

Learn more about Chesterfield

Top reviews in Chesterfield

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent

Frequently Asked Questions

Why book your condo in Chesterfield with Expedia?

How can I find cheap condos in Chesterfield?

What is there to do in Chesterfield near my condo?

Explore a world of travel with Expedia