Title: Chesterfield Cottages from CA $122 | Expedia.ca [Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d6052872.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d6052872.Travel-Guide-VacationRentals)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d6052872.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.ca/Chesterfield.d6052872.Destination-Travel-Guides) ![Chesterfield featuring autumn colours, forests and tranquil scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105801-Chesterfield.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chesterfield Cottage Rentals from CA $122 ## Check prices for these dates In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chesterfield Cottages ![Exterior](https://images.trvl-media.com/lodging/123000000/122270000/122265500/122265441/dfc5e901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/123000000/122270000/122265500/122265441/bf6cee23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/123000000/122270000/122265500/122265441/5aae8bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/123000000/122270000/122265500/122265441/499283d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny house on the Ashuelot river family and pet friendly Swanzey CA $84 CA $122 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Swanzey-Hotels-Tiny-House-On-The-Ashuelot-River-Family-And-Pet-Friendly.h122265441.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) ![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/69000000/68720000/68712000/68711922/8d64a97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro Walpole 10/10 Exceptional (8) "Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frances D. CA $287 CA $354 total includes taxes & fees Nov 18 - Nov 19 [](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=2025-12-01&endDate=2025-12-02®ionId=6052872&adults=2&lodging=COTTAGE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Cottages.d6052872-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Cottages.d6052872-aaCottages.Travel-Guide-Accommodation) ## Top Chesterfield Hotel Reviews ### Latchis Hotel 10/10 Excellent "Staff was outstanding! Informative, kind, engaging, helpful...facility is a wonderful, old building whose history has been respected. Convenient parking lot, and a very walkable area with great restaurants in the area. Looking forward to another stay!" [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ### The Putney Inn 10/10 Excellent "Nice rooms and quite " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ### Riverside Hotel, an Ascend Collection Hotel 10/10 Excellent "Beautiful room, property and staff. I will definitely be back!" [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ### Vikings Villages Resort 10/10 Excellent "A really special place! Like stepping on a movie set!!! We loved it!" [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ### The White House Inn 10/10 Excellent "The room was beautiful and the historic charm was wonderful " [](https://expedia.ca/Wilmington-Hotels-White-House-Inn.h2937372.Hotel-Information) ### Econo Lodge Brattleboro 6/10 Okay "Strip mall next door" [](https://expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.Hotel-Information) ### The Inn At Crumpin Fox 10/10 Excellent "Room was great, we will be back again, favorite place in the valley thus far to stay. " [](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Clean, great staff, great breakfast, warm water pool" [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "The hotel was very busy, so it was noisy. Can't be helped but the wall thermostats work better our rooms did not so I did struggle with the room temp. Too hot or too cold didn't seem to matter what temp it was on. The fan on high speed made a popping sound. No one caught the cobwebs over the headboard. And the lamp didn't work. It was not plugged in but doing so did not make it work. That being said I will stay there again in the future. All of the staff were extremely nice. Just little things, busy, time of year, and things that can be addressed." [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ## Find out more about Chesterfield ## Chesterfield Cottages information | Number of reviews | 7 | | --- | --- | | Accommodation | 55 Cottages | | Lowest Price | CA $122 | | Highest Price | CA $354 | ## 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](https://www.expedia.ca/Asbury-United-Methodist-Church-Chesterfield.d6265749.Vacation-Attraction) is a popular attraction to add to your to-do list. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Monadnock Region](https://www.expedia.ca/3Star-Monadnock-Region-Hotels.s30-0-d553248635975749761.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Keene](https://www.expedia.ca/4Star-Keene-Hotels.s40-0-d6057413.Travel-Guide-Filter-Hotels) - [Hotels near Asbury United Methodist Church](https://www.expedia.ca/Asbury-United-Methodist-Church-Hotels.0-l6265749-0.Travel-Guide-Filter-Hotels) - [Castles in Cheshire County](https://www.expedia.ca/Cheshire-County-Castles.d553248635976430851-aaCastles.Travel-Guide-Accommodation) - [Hotels near Colonial Theatre](https://www.expedia.ca/Colonial-Theatre-Hotels.0-l553248621532666941-0.Travel-Guide-Filter-Hotels) - [Guest Houses in East Swanzey](https://www.expedia.ca/East-Swanzey-Guest-Houses.d553248635976384897-aaGuestHouses.Travel-Guide-Accommodation) - 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