Title: Chesterfield Vacation Rentals from $157: Search Short-Term Rentals | Expedia.com

[Chesterfield Travel Guide](https://expedia.com/Chesterfield.dx6052872)[Hotels in Chesterfield](https://expedia.com/Chesterfield-Hotels.d6052872.Travel-Guide-Hotels)[Flights to Chesterfield](https://expedia.com/Cheap-Flights-To-Chesterfield.d6052872.Travel-Guide-Flights)[Car Rentals in Chesterfield](https://expedia.com/Car-Rentals-In-Chesterfield.d6052872.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.com/Chesterfield.d6052872.Destination-Travel-Guides)

![Chesterfield showing autumn leaves, building ruins and forests](https://images.trvl-media.com/place/6052872/92304bce-f3a0-4703-854a-8556656fcb96.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6052872/92304bce-f3a0-4703-854a-8556656fcb96.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6052872&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6052872&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6052872&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6052872&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chesterfield vacation rentals

![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/7e27ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/512b2604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/c8db5a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely 2nd Floor Apartment

[](https://www.expedia.com/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information)

Greenfield

10/10

Exceptional

(49 reviews)

"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Geoffrey B.

$180 nightly

$201 total

Mar 19 - Mar 20

Total with taxes and fees

[](https://www.expedia.com/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/6cd80eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/fc0d0a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/0a827c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/de082b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wellness Getaway with a Personal Sauna, and Private River Beach!

[](https://www.expedia.com/Newfane-Hotels-Wellness-Getaway-With-A-Personal-Sauna.h106418444.Hotel-Information)

Newfane

10/10

Exceptional

(3 reviews)

"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph P.

$228 nightly

$255 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Newfane-Hotels-Wellness-Getaway-With-A-Personal-Sauna.h106418444.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/c077bee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/b4b598c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/eb8c4f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/1ae2e1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Colrain Spring into Adventure HotTub AirHockey Firepit

[](https://www.expedia.com/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information)

Colrain

9.8/10

Exceptional

(47 reviews)

"Great house for family gatherings "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

John Paul B.

$573 nightly

$640 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/ab38fefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/6eef057c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/7eb92a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/d3aa8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vikings Villages Resort - Double Bed Room

[](https://www.expedia.com/Brattleboro-Hotels-Vikings-Villages-Resort-Double-Bed-Room.h110890615.Hotel-Information)

Guilford

$275 nightly

$279 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Brattleboro-Hotels-Vikings-Villages-Resort-Double-Bed-Room.h110890615.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/5805ee12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/648bcca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/fda99bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/68a2c1c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Studio with a View. Bring your dog, too!

[](https://www.expedia.com/Brattleboro-Hotels-The-Studio-With-A-View-Bring-Your-Dog.h123525991.Hotel-Information)

Brattleboro

10/10

Exceptional

(2 reviews)

"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James M.

$237 nightly

$265 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Brattleboro-Hotels-The-Studio-With-A-View-Bring-Your-Dog.h123525991.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/1f49fb0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/f0bba734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/af3adada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/b112f7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Owl's Nest Treehouse

[](https://www.expedia.com/Alstead-Hotels-Owls-Nest-Treehouse.h111998634.Hotel-Information)

Alstead

10/10

Exceptional

(19 reviews)

"We loved our stay at The Owls Nest! The location was very private, and everything was exceptionally clean. Perfect for a quick weekend getaway to relax. Would highly recommend for a couple looking to enjoy a quiet weekend. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Samantha R.

$302 nightly

$328 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Alstead-Hotels-Owls-Nest-Treehouse.h111998634.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/1ec609e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/5e42b791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b0490e8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b4e38c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake Whitingham & Mount Snow Area Village Apartment

[](https://www.expedia.com/Jacksonville-Hotels-Lake-Whitingham-Mount-Snow-Area-Village-Garden-Apartment-2-BR.h108320042.Hotel-Information)

Whitingham

10/10

Exceptional

(1 review)

"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anicia K.

$273 nightly

$306 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Jacksonville-Hotels-Lake-Whitingham-Mount-Snow-Area-Village-Garden-Apartment-2-BR.h108320042.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/1a650c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/4c5c4ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, video library](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/18ad0df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/953a06fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

[](https://www.expedia.com/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information)

Walpole

10/10

Exceptional

(50 reviews)

"We had a very lovely stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

mary c.

$587 nightly

$637 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/114000000/113540000/113532000/113531990/8e8561f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/114000000/113540000/113532000/113531990/fedd25da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113540000/113532000/113531990/e93e913f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/114000000/113540000/113532000/113531990/63345c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Unit - 101

[](https://www.expedia.com/Wilmington-Hotels-Luxury-ADA-Unit-101.h113531990.Hotel-Information)

Wilmington

10/10

Exceptional

(1 review)

"It was a beautiful place and clean and updated. Plenty of room for our party of four."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael

$594 nightly

$603 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Wilmington-Hotels-Luxury-ADA-Unit-101.h113531990.Hotel-Information)

![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/4c6a2082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8d64a97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

Walpole

10/10

Exceptional

(8 reviews)

"Beautiful cozy cottage. Very clean. Wonderful host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gloria A.

$246 nightly

$266 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/878470a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/128de024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/21da4a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/dcb4e261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

[](https://www.expedia.com/Jacksonville-Hotels-Free-HOT-Breakfast-For-Each-Guest-Everyday-Located-In-Charming-Whitingham.h124515804.Hotel-Information)

Whitingham

8.0/10

Very Good

(2 reviews)

"The was an excellent experience all around! The place is immaculate and exactly as described, stylish and functional for our group of 8\. Appreciated the fireplace, flat screens and PacMan. Check in/out instructions clear and communication w owner quick. The location was convenient for skiing Mt Snow. Jax on Tap a great spot right below for dinner and fun- our crew played shuffleboard and pool. Food was delicious! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Claudia M.

$531 nightly

$594 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Jacksonville-Hotels-Free-HOT-Breakfast-For-Each-Guest-Everyday-Located-In-Charming-Whitingham.h124515804.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/29a39361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/8467145b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/e60f9f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/0c027b4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Hinsdale-Hotels-RESTful-Yurt-In-Charming-Hinsdale-Pet-Friendly-With-Multiple-Hiking-Options.h110594861.Hotel-Information)

Hinsdale

10/10

Exceptional

(10 reviews)

"Yert was perfect and stocked with everything we needed,property owner showed up to make sure we had everything we needed then left us in complete privacy,location was amazing with a great scenic view."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jerry S.

$145 nightly

$157 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Hinsdale-Hotels-RESTful-Yurt-In-Charming-Hinsdale-Pet-Friendly-With-Multiple-Hiking-Options.h110594861.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/019323ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/89c4c4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/31e9eac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/ee17c612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Downtown 12ppl Hot Tub Fire Pit Games

[](https://www.expedia.com/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information)

Keene

9.6/10

Exceptional

(22 reviews)

"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jack P.

$265 nightly

$287 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/a4ec6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w2207h1242x0y0-824667c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/73e1d55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w960h638x0y1-6a5c7328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Family Friendly Hilltop House In Putney Vermont

[](https://www.expedia.com/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information)

Putney

9.4/10

Exceptional

(59 reviews)

"The host and her daughter were lovely and kind and very quick with all communication."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan O.

$244 nightly

$273 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eab00089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/296ae5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/3d81b129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/6cb471c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 14mi to Mt. Snow! Arcade, Private Suite, King Bed!

[](https://www.expedia.com/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information)

Whitingham

10/10

Exceptional

(14 reviews)

"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacklyn D.

$465 nightly

$521 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113400000/113390400/113390345/412e1377_edited_c34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113400000/113390400/113390345/w905h683x60y0-0017d276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113400000/113390400/113390345/w932h683x47y0-0f5dff25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113400000/113390400/113390345/6f7db139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clean & Convenient - Dogs stay free!

[](https://www.expedia.com/Brattleboro-Hotels-Clean-Convenient-Dogs-Stay-Free.h113390345.Hotel-Information)

Brattleboro

$522 nightly

$590 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Brattleboro-Hotels-Clean-Convenient-Dogs-Stay-Free.h113390345.Hotel-Information)

![TV, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/668fb777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/88c2ea85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/b574d618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/1d81a334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Vermont Chalet w/ Sweeping Mountain Views

[](https://www.expedia.com/East-Dover-Hotels-Secluded-Vermont-Chalet-W-Sweeping-Mountain-Views.h123942314.Hotel-Information)

Dover

$453 nightly

$512 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/East-Dover-Hotels-Secluded-Vermont-Chalet-W-Sweeping-Mountain-Views.h123942314.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/bcfc0861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/1ce3fb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/b3ddab44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet Mount Snow/Stratton Skiing/hiking

[](https://www.expedia.com/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

East Dover

9.8/10

Exceptional

(10 reviews)

"Easy to find! Clean! Cozy!! Would definitely stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roy-michael G.

$361 nightly

$408 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/9530dfe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/40c2e2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/17e097bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/c459a4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning Glass House nestled in the Vermont wilderness!

[](https://www.expedia.com/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information)

Guilford

10/10

Exceptional

(1 review)

"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Grant D.

$353 nightly

$396 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/262afaed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/41130fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/d458659b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/c9f7c522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy apt in beautiful secluded spot 15 mins from Mt Snow

[](https://www.expedia.com/East-Dover-Hotels-Cozy-Apt-In-Beautiful-Secluded-Spot-15-Mins-From-Mt-Snow.h113155266.Hotel-Information)

Dover

10/10

Exceptional

(4 reviews)

"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erica H.

$183 nightly

$207 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/East-Dover-Hotels-Cozy-Apt-In-Beautiful-Secluded-Spot-15-Mins-From-Mt-Snow.h113155266.Hotel-Information)

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](https://expedia.com/Hotel-Search?startDate=2026-03-29&endDate=2026-03-30&regionId=6052872&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APARTMENT)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=CONDO)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=CHALET)

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## Top Chesterfield Hotel Reviews

![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/49e216b5_y.jpg)

### Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"Everything was perfect!"

[](https://expedia.com/Keene-Hotels-Holiday-Inn-Express-Keene.h14439.Hotel-Information)

![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca_y.jpg)

### Best Western Plus Keene Hotel

2/10 Terrible

"TVs didn’t work. Shower was broken. Heater was very loud and falling out of the wall. Computers were down my entire stay and they disable my door cards by accident. It may be cheap but you def get what you pay for. "

[](https://expedia.com/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information)

![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c_y.jpg)

### The Putney Inn

10/10 Excellent

"We were doing a ski trip to Mount Snow and this was an excellent low-cost room for a single night. No frills and a good price. Coffee and simple breakfast (yogurt, cereal) was available the next morning on our way out the door. "

[](https://expedia.com/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information)

![Riverside Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg)

### Riverside Hotel, an Ascend Collection Hotel

8/10 Good

"The views are beautiful and the hotel is very clean. The beds are quite uncomfortable, at least for us (very firm mattress). No food available on site during nearly all of our stay. Does have a good mini fridge if you shop ahead. Very friendly staff. "

[](https://expedia.com/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information)

![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/50bc8764_y.jpg)

### Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"Nice, quiet, clean spot handy to I91."

[](https://expedia.com/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information)

![The White House Inn](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/3499e03e_y.jpg)

### The White House Inn

10/10 Excellent

"With a a restaurant/bar on site and the “speak easy” down stairs to play pool, sit by the fire, play games. It’s truly gave the feel of a historic resort more than just a lovely inn."

[](https://expedia.com/Wilmington-Hotels-White-House-Inn.h2937372.Hotel-Information)

![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d_y.jpg)

### Hampton Inn Brattleboro

8/10 Good

"Check in was easy. After first night the internet shut down. Came back on late the second night. This location is under renovations. Strong paint smell and the worker was there until 8pm at night drilling and sawing. Since our plans fell apart, we left two days early. I'm sure when the renovations are done, it will be pleasant."

[](https://expedia.com/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information)

![Courtyard by Marriott Keene Downtown](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9384b42d_y.jpg)

### Courtyard by Marriott Keene Downtown

10/10 Excellent

"Quiet and convenient location. Loved having a microwave in my room. I wasn't in the mood for wating out so a trip to the neighbouring supermarket set me up perfectly."

[](https://expedia.com/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information)

![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg)

### Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Everything was great. Clean rooms, friendly staff, good stay.."

[](https://expedia.com/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information)

## Find out more about Chesterfield

**Everything you need to know about Chesterfield vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chesterfield vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chesterfield rentals**

At Expedia, we put the best Chesterfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Chesterfield ](https://expedia.com/Chesterfield-Private-Vacation-Homes.d6052872-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Chesterfield ](https://expedia.com/Chesterfield-Cottages.d6052872-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Chesterfield ](https://expedia.com/Chesterfield-Apartments.d6052872-aaApartments.Travel-Guide-Accommodation)
- [B&B in Chesterfield ](https://expedia.com/Chesterfield-Bed-And-Breakfast.d6052872-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Chesterfield ](https://expedia.com/Chesterfield-Cabins.d6052872-aaCabins.Travel-Guide-Accommodation)
- [Resorts in Chesterfield ](https://expedia.com/Chesterfield-Resorts.d6052872-aaResorts.Travel-Guide-Accommodation)
- [Chalets in Chesterfield ](https://expedia.com/Chesterfield-Chalets.d6052872-aaChalets.Travel-Guide-Accommodation)
- [Farmstay in Chesterfield ](https://expedia.com/Chesterfield-Agritourism.d6052872-aaAgritourism.Travel-Guide-Accommodation)
- [Condo Rentals in Chesterfield ](https://expedia.com/Chesterfield-Condos.d6052872-aaCondos.Travel-Guide-Accommodation)
- [Motels in Chesterfield ](https://expedia.com/Chesterfield-Motels.d6052872-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Chesterfield ](https://expedia.com/Chesterfield-Guest-Houses.d6052872-aaGuestHouses.Travel-Guide-Accommodation)
- [Lodges in Chesterfield ](https://expedia.com/Chesterfield-Lodges.d6052872-aaLodges.Travel-Guide-Accommodation)
- [Villas in Chesterfield ](https://expedia.com/Chesterfield-Villas.d6052872-aaVillas.Travel-Guide-Accommodation)
- [RV Parks in Chesterfield ](https://expedia.com/Chesterfield-RV-Parks.d6052872-aaRVParks.Travel-Guide-Accommodation)
- [Inns in Chesterfield ](https://expedia.com/Chesterfield-Inns.d6052872-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Chesterfield?

### What are some of the best vacation home rentals in Chesterfield?

### What can I see and do in Chesterfield?

### What are vacation rentals like in Chesterfield?