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

Search Chesterfield Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chesterfield cottages

A house with a deck, surrounded by trees and a grassy slope.

1. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
$366 nightly
The price is $403
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A spacious living room with a checkered sofa, a grey sofa, and a patterned rug. There is a staircase leading to another level, and a dining area with a table and chairs.

2. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
$385 nightly
The price is $417
Sep 15 - Sep 16
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

The White House Inn

The White House Inn

8/10 Good
"Dinner was wonderful. But the free breakfast was very lacking. Toast was burnt. Fruit looked a few days old. Beautiful location, Beautiful room."
kerrilyn 1-night trip
Posted 4 hours ago
The White House Inn

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
1
Accommodation
60 Cottages
Lowest Price
$403
Highest Price
$403

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.

Explore a world of travel with Expedia