Search and Rent Chesterfield Condos

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In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterfield

Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (750)
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
$134 nightly
The price is $148
Jan 3 - Jan 4, 2026
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
Exterior detail
The Covered Bridge Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1000)
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
United States
Megan
$86 nightly
The price is $95
Jan 9 - Jan 10, 2026
Total with taxes and fees
The Covered Bridge Inn
Front of property
The Inn At Crumpin Fox

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (345)
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
$141 nightly
The price is $158
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Inn At Crumpin Fox
Free breakfast
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (930)
"Good breakfast, great staff and very good location "
United States
Valdeci
$147 nightly
The price is $161
Jan 16 - Jan 17, 2026
Total with taxes and fees
Hampton Inn Brattleboro
Porch
Harvest Barn Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
$141 nightly
The price is $154
Jan 3 - Jan 4, 2026
Total with taxes and fees
Harvest Barn Inn
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1000)
"The room was okay for a quick stop to rest. "
United States
Janice
$75 nightly
The price is $83
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Putney Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
$123 nightly
The price is $134
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Carriage Barn Inn
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
$129 nightly
The price is $140
Jan 1 - Jan 2, 2026
Total with taxes and fees
Best Western Plus Keene Hotel
Garden
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (16)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
$129 nightly
The price is $141
Jan 4 - Jan 5, 2026
Total with taxes and fees
Four Columns Inn
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very Good, (971)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
$114 nightly
The price is $124
Jan 1 - Jan 2, 2026
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior
The One Cat B&B

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
$128 nightly
The price is $141
Jan 21 - Jan 22, 2026
Total with taxes and fees
The One Cat B&B
Interior detail
The White House Inn

The White House Inn

The White House Inn
3.5 star property
Wilmington
9.2 out of 10, Wonderful, (268)
"We stayed at the White House in two weekends in a row while our house was under construction. We loved that they had music until 9 and that the room was clean and the beds were comfortable. The staff made sure we had everything we needed. We would definitely recommend."
United States
Stacy
$184 nightly
The price is $202
Jan 4 - Jan 5, 2026
Total with taxes and fees
The White House Inn
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
$180 nightly
The price is $195
Jan 6 - Jan 7, 2026
Total with taxes and fees
Fairfield Inn & Suites by Marriott Keene Downtown
Front of property
Colonel Williams Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
$143 nightly
The price is $158
Jan 14 - Jan 15, 2026
Total with taxes and fees
Colonel Williams Inn
Hiking
Latchis Hotel

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (841)
"Great stay"
United States
Jason
$118 nightly
The price is $130
Jan 6 - Jan 7, 2026
Total with taxes and fees
Latchis Hotel
Front of property
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (476)
"Room looked good. Wish they have shampoo. Only one soap. Nice shower pressure. Would visit again "
United States
Miles
$99 nightly
The price is $109
Jan 1 - Jan 2, 2026
Total with taxes and fees
Black Mountain Inn
Sundeck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (633)
"Clean room, beautiful location"
United States
Marcie
$161 nightly
The price is $175
Jan 6 - Jan 7, 2026
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel
Exterior
The Burrell House

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
$192 nightly
The price is $209
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Burrell House
Free daily on-the-go breakfast
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1001)
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
$149 nightly
The price is $164
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
In-room safe, desk, blackout drapes, iron/ironing board
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1000)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
$105 nightly
The price is $113
Jan 18 - Jan 19, 2026
Total with taxes and fees
Days Inn by Wyndham Keene NH
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

Colonial Motel And Spa

Colonial Motel And Spa

10/10 Excellent
"Great location and service "
Paul 2-night trip
Posted 3 days ago
Colonial Motel And Spa

Find out more about Chesterfield

Chesterfield Condo Rentals information

Number of reviews
11,942
Accommodation
7 Condo Rentals
Lowest Price
$83
Highest Price
$209

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.

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