Chesterfield Holiday Rentals, New Hampshire: Private House Rentals

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

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Go beyond your typical stay in Chesterfield

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Our top choices for Chesterfield hotels

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

A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.

1. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Morgan

3.382.022 ₫

3.720.224 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

A building entrance with a white door, number 959, and a small porch area decorated with pumpkins, flowers, and scarecrows.

A hotel room with a bed, two bedside lamps, a nightstand, a chair, and a small table.

A cozy reading area with wooden chairs, a table with newspapers, and potted plants.

2. Black Mountain Inn

Brattleboro

Robert

3.537.373 ₫

3.891.109 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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.

A hotel room with two beds, a desk, a chair, a television, a dresser, and a door leading to a bathroom.

3. Colonial Motel

Brattleboro

James

2.145.951 ₫

2.360.546 ₫ total

includes taxes & fees

25 Aug - 26 Aug

A dining area with a table and four chairs, a painting of a covered bridge, and a painting of a red building.

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

A multi-story motel with a parking lot, several vehicles parked, and a tree in the foreground.

A sign for The Covered Bridge Inn with a welcome message.

4. The Covered Bridge Inn

Brattleboro

VINCENT JOEL

1.838.566 ₫

2.022.423 ₫ total

includes taxes & fees

26 Aug - 27 Aug

A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.

A spacious lobby with modern furniture, a large digital map display, and a high ceiling with geometric lighting.

5. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Marnie

4.648.648 ₫

5.113.513 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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.

A living room with a sofa, armchair, and round table, a bedroom with a bed and nightstands, and large windows with curtains.

6. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Pauline

3.972.244 ₫

4.309.884 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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 banquet hall with round tables, chairs, and a staircase.

A hotel lobby with a reception desk, seating area, and a large window.

7. Latchis Hotel

Brattleboro

Stark

2.914.076 ₫

3.205.483 ₫ total

includes taxes & fees

25 Aug - 26 Aug

A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.

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.

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

8. Hampton Inn Brattleboro

Brattleboro

Timothy

2.971.478 ₫

3.268.626 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.

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.

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

James

3.133.920 ₫

3.400.303 ₫ total

includes taxes & fees

1 Sept - 2 Sept

A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

A grassy field with a playground and trees in the background.

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

A motel with a parking lot, a covered walkway, and a staircase leading to the entrance.

10. The Putney Inn

Putney

JANE

2.844.032 ₫

3.128.435 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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 gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

A covered outdoor area with a wooden deck, white railings, and string lights.

11. Best Western Plus Keene Hotel

Keene

Karen

3.891.284 ₫

4.222.174 ₫ total

includes taxes & fees

25 Aug - 26 Aug

A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.

A bar area with a fireplace, seating, and a TV.

A bar area with a dark wooden bar, multiple bar stools, and a large screen displaying the hotel name.

12. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

James

4.689.128 ₫

5.087.704 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

A conference table set for a meeting with chairs and folded red napkins.

A gazebo with a red roof and white walls, surrounded by trees and a brick building.

A brick building with a red awning and a sign that reads "The Inn."

13. The Inn At Crumpin Fox

Bernardston

Christopher

4.241.238 ₫

4.737.442 ₫ total

includes taxes & fees

25 Aug - 26 Aug

A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.

A flat-screen TV mounted on a wall displaying a streaming service interface.

A room with a round table and two leather chairs, a window with curtains, and a view of a parking lot outside.

A grassy area with picnic tables and a clock tower.

14. Windmill Motel Restaurant

Bernardston

Robert

3.173.094 ₫

3.544.345 ₫ total

includes taxes & fees

25 Aug - 26 Aug

A wooden table set with plates, cutlery, and a folded napkin.

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.

A bench in front of an apple tree with ripe apples.

15. The Carriage Barn Inn

Keene

Jonathan

3.816.279 ₫

4.140.663 ₫ total

includes taxes & fees

25 Aug - 26 Aug

A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".

An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.

A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.

16. Courtyard by Marriott Keene Downtown

Keene

Deborah

4.689.128 ₫

5.087.704 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

A covered outdoor seating area with tables and chairs, overlooking a residential street with houses and a road.

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.

17. The Burrell House

Keene

Justin

3.277.213 ₫

3.654.092 ₫ total

includes taxes & fees

26 Aug - 27 Aug

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

A wooden log cabin with a snow-covered entrance and a wooden fence in a snowy forest.

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.

18. Vikings Villages Resort

Guilford

Juli

3.914.566 ₫

4.565.559 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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 hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.

A conference room with a black table, wooden chairs, a mounted TV, and a decorative mirror.

19. Days Inn by Wyndham Keene NH

Keene

Michael

2.530.902 ₫

2.746.029 ₫ total

includes taxes & fees

16 Sept - 17 Sept

A large white building with a stone wall and a lawn covered in fallen leaves.

A long banquet table set up in a rustic barn with string lights and paper lanterns.

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

A large white house with a dark roof, surrounded by snow-covered ground and trees.

20. Colonel Williams Inn

Brattleboro

Robert

4.113.270 ₫

4.524.597 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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Stay near popular Chesterfield attractions

Asbury United Methodist Church

You can learn about the history of Chesterfield when you stop by Asbury United Methodist Church. Amble around the area's riverfront or seek out its ski slopes.

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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.

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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 in a forest with autumn leaves.

Top Chesterfield Hotel Reviews

The White House Inn

8/10 Good

"Very kind staff and neat and clean"

Courtyard by Marriott Keene Downtown

10/10 Excellent

"Everything was great!! Beds were super comfortable."

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good

"The room was clean and stocked with the amenities expected, including a fridge and a microwave. Staff was very helpful and kind on check in. Breakfast was a standard continental. Not the best food but there was an array of options."

Colonial Motel

8/10 Good

"X"

The Putney Inn

8/10 Good

"I would recommend the Putney inn"

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent

"The Riverside is a lovely place to stay when in the Brattleboro VT area. The rooms are spacious and exceptionally clean. View of the river makes for a nice setting. The hotel is very quiet. Staff are helpful and welcoming."

Windmill Motel Restaurant

10/10 Excellent

"Great place and convenience store was a nice touch"

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent

"Right in the middle of town. Very comfortable. Nice breakfast in the morning. Liked the candy in the lobby."

Latchis Hotel

8/10 Good

"The art deco building is gorgeous. I applaud the non-profit organization that saved, renovated and maintains this exceptional building. I very much appreciated the original bathroom fixtures. The hotel really gives you a taste of what it might have been like to travel back in the 1930-40s. On the downside, my experience was not the best: When I arrived, the front desk lady said something like: "I'll be right with you". Two minutes later, she came to the front desk joking about having problems with her Emails. Not acceptable! You should pause your Email activity when someone is waiting in the lobby. My wife and I were looking forward to a drink at the hotel bar. The website indicated that the bar was open, and a note on the door confirmed. There was nobody there. Money and a lady's purse were spread out on the bar. We were told at the front desk that the people running the bar for them decided not to open that evening. Not acceptable. The next morning I took a lukewarm shower, as it took about ten minutes for the water to become warm enough, By then I was done and my feet were in about 5" of dirty water because the drain was clogged. We were also told that if we did not turn in our brass key, they would charge us $75 to replace it. When walked down to the lobby, there was a sign stating that front desk duty started at 9:00."

More cheap stays in Chesterfield

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

2.530.902 ₫

2.746.029 ₫ total

16 Sept - 17 Sept

includes taxes & fees

7/10 Good! (1,004 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

2.914.076 ₫

3.205.483 ₫ total

25 Aug - 26 Aug

includes taxes & fees

8.6/10 Excellent! (965 reviews)

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

2.971.478 ₫

3.268.626 ₫ total

8 Sept - 9 Sept

includes taxes & fees

8.2/10 Very good! (1,015 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

3.133.920 ₫

3.400.303 ₫ total

1 Sept - 2 Sept

includes taxes & fees

8.6/10 Excellent! (1,013 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

3.382.022 ₫

3.720.224 ₫ total

31 Aug - 1 Sept

includes taxes & fees

8.6/10 Excellent! (849 reviews)

Holiday Inn Express Hotel & Suites Brattleboro by IHG

100 Chickering Drive Brattleboro VT

4.648.648 ₫

5.113.513 ₫ total

13 Sept - 14 Sept

includes taxes & fees

8.8/10 Excellent! (1,012 reviews)

Hotels in Chesterfield with star rating

Frequently asked questions

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.

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Find hotels in Chesterfield, NH from 1.783.984 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chesterfield

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chesterfield hotels

1. Comfort Inn & Suites Brattleboro I-91

2. Black Mountain Inn

3. Colonial Motel

4. The Covered Bridge Inn

5. Holiday Inn Express Hotel & Suites Brattleboro by IHG

6. Riverside Hotel, an Ascend Collection Hotel

7. Latchis Hotel

8. Hampton Inn Brattleboro

9. Keene Elm City Hotel, an Ascend Collection Hotel

10. The Putney Inn

11. Best Western Plus Keene Hotel

12. Fairfield Inn & Suites by Marriott Keene Downtown

13. The Inn At Crumpin Fox

14. Windmill Motel Restaurant

15. The Carriage Barn Inn

16. Courtyard by Marriott Keene Downtown

17. The Burrell House

18. Vikings Villages Resort

19. Days Inn by Wyndham Keene NH

20. Colonel Williams Inn

Stay near popular Chesterfield attractions

Asbury United Methodist Church

Chesterfield Town Hall

Learn more about Chesterfield

Top Chesterfield Hotel Reviews

The White House Inn

Courtyard by Marriott Keene Downtown

Keene Elm City Hotel, an Ascend Collection Hotel

Colonial Motel

The Putney Inn

Riverside Hotel, an Ascend Collection Hotel

Windmill Motel Restaurant

Fairfield Inn & Suites by Marriott Keene Downtown

Latchis Hotel

More cheap stays in Chesterfield

Days Inn by Wyndham Keene NH

Latchis Hotel

Hampton Inn Brattleboro

Keene Elm City Hotel, an Ascend Collection Hotel

Comfort Inn & Suites Brattleboro I-91

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Hotels in Chesterfield with star rating

Frequently asked questions

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