Title: Chesterfield Vacation Rentals from CA $217: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2026-07-17&endDate=2026-07-19&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

![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)

![Interior](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/90945353.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.ca/Hinsdale-Hotels-RESTful-Yurt-In-Charming-Hinsdale-Pet-Friendly-With-Multiple-Hiking-Options.h110594861.Hotel-Information)

Hinsdale

10/10

Exceptional

(11 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.

CA $124

CA $217 total

includes taxes & fees

Mar 30 - Mar 31

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

![Living area](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/75d33052.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)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/d458659b.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.ca/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.

CA $117

CA $283 total

includes taxes & fees

Mar 31 - Apr 1

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

![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/c8db5a9a.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)

### Lovely 2nd Floor Apartment

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

Greenfield

10/10

Exceptional

(50 reviews)

"Very clean, cozy and lots of nice plants! "

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

Mary

CA $160

CA $279 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/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/de082b20.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)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/w956h736x34y34-3e10a6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/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.

CA $186

CA $353 total

includes taxes & fees

Mar 31 - Apr 1

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

![Exterior](https://images.trvl-media.com/lodging/122000000/121770000/121762500/121762412/2839dc48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121770000/121762500/121762412/56a92958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121770000/121762500/121762412/afc852a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121770000/121762500/121762412/6211d6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Central Large 2-bedrooms with office in Keene

[](https://www.expedia.ca/Keene-Hotels-Central-Large-3-Bedroom-Apartment-In-Keene.h121762412.Hotel-Information)

Keene

10/10

Exceptional

(2 reviews)

"Friendly hosts and excellent location to walk to downtown."

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

Joshua

CA $237

CA $292 total

includes taxes & fees

Apr 2 - Apr 3

[](https://www.expedia.ca/Keene-Hotels-Central-Large-3-Bedroom-Apartment-In-Keene.h121762412.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)

![Game room](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/eb8c4f2d.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)

![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)

### Spacious 5BR w/ Hot Tub & Games

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

Colrain

9.8/10

Exceptional

(48 reviews)

"Great house for family gatherings "

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

John Paul B.

CA $392

CA $899 total

includes taxes & fees

Mar 29 - Mar 30

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

![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/w1125h1933x0y49-6292efb5.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)

###  Family Friendly Hilltop House In Putney Vermont

[](https://www.expedia.ca/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.

CA $214

CA $406 total

includes taxes & fees

Apr 9 - Apr 10

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.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)

### Chalet Mount Snow/Stratton Skiing/hiking

[](https://www.expedia.ca/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.

CA $204

CA $661 total

includes taxes & fees

Apr 19 - Apr 20

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

CA $183

CA $375 total

includes taxes & fees

Apr 7 - Apr 8

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

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/14ace880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/0780f54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/70217bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/b15a729a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

[](https://www.expedia.ca/Newfane-Hotels-Outdoor-Adventure-Haven-14-Mi-To-Mount-Snow-Skiing.h120618609.Hotel-Information)

Newfane

CA $311

CA $795 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Newfane-Hotels-Outdoor-Adventure-Haven-14-Mi-To-Mount-Snow-Skiing.h120618609.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)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/0997d6b6.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)

### Lake Whitingham & Mount Snow Area Village Apartment

[](https://www.expedia.ca/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.

CA $193

CA $422 total

includes taxes & fees

Apr 1 - Apr 2

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

![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)

![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/b4c71f0d.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)

![Exterior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/a6be84e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Keene

9.6/10

Exceptional

(22 reviews)

"Nice house in a nice location. "

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

Rob B.

CA $211

CA $432 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.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/124000000/123950000/123942400/123942314/1d81a334.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/w1280h852x0y1-a2dcac1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Vermont Chalet w/ Sweeping Mountain Views

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

Dover

CA $196

CA $718 total

includes taxes & fees

Mar 30 - Mar 31

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

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/07d1d9b9.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)

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

### Vikings Villages Resort - Double Bed Room

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

Guilford

CA $311

CA $384 total

includes taxes & fees

Mar 29 - Mar 30

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

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/e3b7abc8.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.ca/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information)

Walpole

10/10

Exceptional

(51 reviews)

"We had a very lovely stay. "

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

mary c.

CA $399

CA $834 total

includes taxes & fees

Mar 30 - Mar 31

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/ab414fef.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)

### Owl's Nest Treehouse

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

Alstead

10/10

Exceptional

(20 reviews)

"Amazing place, cozy, clean and organized. I loved it and I want to come back again."

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

Alex F.

CA $380

CA $469 total

includes taxes & fees

Mar 31 - Apr 1

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

![Property grounds](https://images.trvl-media.com/lodging/122000000/121180000/121175600/121175575/6167fb25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121180000/121175600/121175575/d345c5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121180000/121175600/121175575/4f5d841b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/122000000/121180000/121175600/121175575/09f47c4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Yurt Oasis in the woods of Hinsdale, NH

[](https://www.expedia.ca/Hinsdale-Hotels-Yurt-Oasis-In-The-Woods-Of-Hinsdale.h121175575.Hotel-Information)

Hinsdale

CA $143

CA $230 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Hinsdale-Hotels-Yurt-Oasis-In-The-Woods-Of-Hinsdale.h121175575.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)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/38754554.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)

![Game room](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/128de024.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.ca/Jacksonville-Hotels-Free-HOT-Breakfast-For-Each-Guest-Everyday-Located-In-Charming-Whitingham.h124515804.Hotel-Information)

Whitingham

8.8/10

Excellent

(3 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.

CA $453

CA $824 total

includes taxes & fees

Mar 29 - Mar 30

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/516bcaba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/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.

CA $276

CA $703 total

includes taxes & fees

Apr 13 - Apr 14

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

![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)

![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)

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

[](https://www.expedia.ca/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.

CA $285

CA $352 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.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.ca/Hotel-Search?startDate=2026-04-10&endDate=2026-04-11&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.ca/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CABIN)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=VACATION_HOME)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+New+Hampshire%2C+United+States+of+America&regionId=6052872&latLong=42.88728%2C-72.470718&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CHALET)

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## Top Chesterfield Hotel Reviews

![Econo Lodge Brattleboro South](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/de359926_y.jpg)

### Econo Lodge Brattleboro South

2/10 Terrible

"Do not stay here. Inhabitable, unsafe. Had to leave. Fire alarms taken off wall. Tissue covering sprinklers. Light fixtures broken. Walls dirty. Bed sheets and pillows dirty. "

[](https://expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.Hotel-Information)

![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8_y.jpg)

### Latchis Hotel

10/10 Excellent

"Very quaint, great attention to detail. We appreciated the easy access to the Theater!"

[](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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

"It was a beautiful inn. Even in early spring when it's mud season in Vermont. The restaurant was amazing. Really good wine and Italian dishes. The staff was really friendly. The rooms were very comfortable with a large bathroom and walk in shower. We will certainly go back. "

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

![Farm Road Estate](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/ef464910_y.jpg)

### Farm Road Estate

10/10 Excellent

"Charming, comfortable, peaceful, relaxing. I’ll definitely be back!"

[](https://expedia.ca/West-Dover-Hotels-Farm-Road-Estate.h88730696.Hotel-Information)

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

### The Putney Inn

10/10 Excellent

"Clean, quiet, felt safe, staff was friendly, reasonably priced."

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

![Days Inn by Wyndham Keene NH](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg)

### Days Inn by Wyndham Keene NH

2/10 Terrible

"Our room for the night was gross. The blankets had brown smears on them, the bathroom had hair and dirt everywhere, the tv wouldn't change channels, and to top it off the fire alarms battery compartment was open with absolutely no batteries in it. This place was cheaper for the area, so I didn't have high hopes for it to begin with, but it was much worse than expected. Will not recommend and will not be back. "

[](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.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

8/10 Good

"Room was fine. Only stayed one night for a quick trip. Didn't realize that the restaurant was closed on Sundays. Was looking for a meal after a long drive, but there were plenty of places to eat in the area. "

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

![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41_y.jpg)

### The Covered Bridge Inn

6/10 Okay

"Good job"

[](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information)

![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg)

### Colonial Motel And Spa

2/10 Terrible

"What a dump"

[](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information)

## Find out more about Chesterfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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

## Frequently asked questions

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