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

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
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

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (707 reviews)
"Loved view of the river"
United States
Steve
$147 nightly
The price is $160
Nov 23 - Nov 24
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel
A large, yellow building with a sign for Hampton Inn. There are cars parked in front and a clear sky.

2. Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,001 reviews)
"Great stay in a newly renovated room. Clean and comfortable. I have stayed before the renovation and will happily stay again."
United States
Sharon
$115 nightly
The price is $126
Nov 15 - Nov 16
Total with taxes and fees
Hampton Inn Brattleboro
A multi-story hotel with a stone facade and a flat roof.

3. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (899 reviews)
"Great welcome, nice and convenient location. Clean, quiet, updated room with a comfortable bed."
United States
Kamilla
$112 nightly
The price is $124
Nov 15 - Nov 16
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
A hotel with a covered entrance, a clear sky, and a tree in the foreground.

4. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,002 reviews)
"Stayed one night. Staff was very friendly. Clean rooms, easy parking, nice breakfast."
United States
Timothy
$139 nightly
The price is $153
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A hotel with a clock tower, a parking lot, and a well-maintained garden.

5. Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.6 out of 10, Good, (531 reviews)
"The front desk were very helpful"
United States
Ron
$103 nightly
The price is $113
Nov 8 - Nov 9
Total with taxes and fees
Black Mountain Inn
A multi-story building with a prominent sign for 'Hotel Latchis' indicating it houses a coffee shop, theater, and ballroom.

6. Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (1,001 reviews)
"Hotel was great with extremely helpful, engaging and friendly staff."
United States
Erik
$113 nightly
The price is $124
Nov 9 - Nov 10
Total with taxes and fees
Latchis Hotel
A motel with a parking lot, a covered walkway, and a staircase leading to the entrance.

7. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"Great location and wonderful staff! I love staying here every year!"
United States
Kristen
$81 nightly
The price is $89
Dec 8 - Dec 9
Total with taxes and fees
The Putney Inn
A motel with a central staircase, multiple rooms, and a parking lot.

8. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (845 reviews)
"If you are looking for a clean place to rest your head for the night this place is it!"
United States
Cara
$62 nightly
The price is $68
Nov 10 - Nov 11
Total with taxes and fees
Travelodge by Wyndham Brattleboro VT
A motel with multiple floors, each with balconies and windows.

9. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.4 out of 10, (115 reviews)
"Value for money. Clean and conveniently located. Friendly staff."
United States
Swaraj
$95 nightly
The price is $105
Nov 8 - Nov 9
Total with taxes and fees
Colonial Motel
A multi-story motel with a parking lot, several vehicles parked, and a tree in the foreground.

10. The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.2 out of 10, Good, (1,002 reviews)
"Good location. About what one might expect in a budget motel."
United States
Rick
$130 nightly
The price is $143
Dec 7 - Dec 8
Total with taxes and fees
The Covered Bridge Inn
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

11. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
$267 nightly
The price is $294
Nov 8 - Nov 9
Total with taxes and fees
Inn on Putney Road
A large, two-story house with a snow-covered driveway and surrounding trees.

12. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.4 out of 10, Exceptional, (106 reviews)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
Nov 8 - Nov 9
Total with taxes and fees
Chesterfield Inn
A Days Inn with a brick facade, a central entrance, and a parking lot.

13. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,002 reviews)
"convenient and safe place to stay while on a drivng vacation through New England"
United States
CHERYL
$92 nightly
The price is $100
Nov 10 - Nov 11
Total with taxes and fees
Days Inn by Wyndham Keene NH
The exterior of the Keene Elm City Hotel with a parking lot in front.

14. 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, (1,003 reviews)
"Excellent stay"
United States
Lisa
$133 nightly
The price is $144
Nov 8 - Nov 9
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
A motel with a clock tower and a sign reading "EconoLodge."

15. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (699 reviews)
"I asked him on the front desk if I get a coffee machine but hi said no wen i order online they said breakfast is available but is not the guy in front desk was rude"
United States
Luis
$99 nightly
The price is $109
Dec 7 - Dec 8
Total with taxes and fees
Econo Lodge Brattleboro South
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

16. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,004 reviews)
"Great place to go"
United States
Ruddy
$142 nightly
The price is $154
Nov 10 - Nov 11
Total with taxes and fees
Best Western Plus Keene Hotel
A two-story wooden building with a garage, a covered outdoor area, and a car parked in front.

17. Otherland Hotel

Otherland Hotel
2.5 star property
Newfane
9.6 out of 10, Exceptional, (236 reviews)
"Love the Nordik style accommodations and very comfortable bed!"
United States
Debi
$157 nightly
The price is $171
Nov 8 - Nov 9
Total with taxes and fees
Otherland Hotel
A rustic cabin with a covered porch, a small shed, and outdoor seating.

18. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$142 nightly
The price is $154
Nov 12 - Nov 13
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

19. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (431 reviews)
"Comfortable, clean, friendly staff, great breakfast"
United States
Dayle
$158 nightly
The price is $171
Nov 28 - Nov 29
Total with taxes and fees
Hampton Inn & Suites Keene
A historic brick building with a porch and a sign reading "Burrell House."

20. The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (189 reviews)
"The Burrell House is a lovely historic home convenient to downtown Keene. The room was very clean and the bed super comfortable. There is no staff but it worked fine for my stay."
United States
Carol
$153 nightly
The price is $166
Nov 16 - Nov 17
Total with taxes and fees
The Burrell 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.
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Top Chesterfield Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"I got there a little early and was able to check in. Room was great. Price was great. Recommended if you're headed to the Putney/Brattleboro area."
Sean 1-night trip
Posted 4 hours ago
The Putney Inn

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
5,169
Accommodation
60 Cottages
Lowest Price
$68
Highest Price
$327

Frequently asked questions

Why book your cottage in Chesterfield with Expedia?
Reserving a cottage in Chesterfield is as easy as clicking on your travel dates and selecting your ideal place for a getaway in nature. From luxurious retreats to inexpensive stays and cottages that come with amenities like a kitchenette, Expedia has something for all traveler styles. As for epic deals? We've got them too!
How can I find cheap cottages in Chesterfield?
With Expedia's useful filter tool, comparing cheap cottages in Chesterfield is a cinch. To discover accommodations that'll make your hip pocket happy, narrow down your search by budget, star rating and amenities.
What is there to do in Chesterfield near my cottage?
Once you've settled into your hotel, set out and explore the incredible things Chesterfield has for you to experience. Asbury United Methodist Church is a popular attraction to add to your to-do list.

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