Title: Chesterfield Vacation Home Rentals from CA $282: Search Top Private Vacation Homes for Rent | 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) # Chesterfield Vacation Rentals ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chesterfield Vacation Homes ![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/a4ec6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/48ea3a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/3315ad26.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 Putney 9.4/10 Exceptional (56) "The property was beautiful--great views, super peaceful, and fabulous hosts. " CA $158 CA $335 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/79a253e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/d695e72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/70342e8e.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 Greenfield 10/10 Exceptional (39) "Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. " CA $163 CA $282 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/78692cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/fd35a312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/4702110d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/f112c530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls Colrain 10/10 Exceptional (4) "This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. " CA $210 CA $485 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Colrain-Hotels-Couples-2-Bedroom-Retreat-Hot-Tub-Air-Hockey-Close-To-ShelburneFalls.h113519074.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/6ba9f20d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/7ec1e2c6.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) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eca16f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed Whitingham 10/10 Exceptional (14) "Great property, plenty of space and room for all. Location is ideal" CA $273 CA $698 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/d9a32dde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/16a722ec.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! Guilford 10/10 Exceptional (1) "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." CA $242 CA $643 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/a9ea01f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/4e1069ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/8ebf8854.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) ### Downtown Hot Tub Escape Keene 9.6/10 Exceptional (20) "Nice house in a nice location. " CA $315 CA $558 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/458d1d2d.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) ![Smart TV, books](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/8fcd0ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/3bdb7bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit Colrain 9.8/10 Exceptional (37) "Great place and convenient to get to and from Berkshire East." CA $385 CA $882 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/7d6a1254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/bf925c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/0c3d5316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/314d0c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MtSnow\* HotTub\* Pool \* AirHockey\*PingPong \* Darts Wilmington CA $257 CA $868 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Wilmington-Hotels-MtSnow-HotTub-Pool-AirHockeyPingPong-Darts.h119097866.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/ae0971bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/f38617c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/4e846ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/bf6afd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Home Walk to Downtown! Keene 10/10 Exceptional (1) "Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even... CA $437 CA $1,020 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.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=2025-10-26&endDate=2025-10-27®ionId=6052872&adults=2&lodging=VACATION_HOME&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-Private-Vacation-Homes.d6052872-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Private-Vacation-Homes.d6052872-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chesterfield Hotel Reviews ![The White House Inn](//images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/fe9c2db1_y.jpg) ### The White House Inn 10/10 Excellent "Beautifully restored inn, it could be in a Hallmark movie, loved it." [](https://expedia.ca/Wilmington-Hotels-White-House-Inn.h2937372.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 "The staff was helpful and friendly. The breakfast was good with many choices available. The room was good and the bed was comfortable. My wife would have liked to have a hair dryer available." [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Excellent staff" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](//images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "Clean room" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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 "Excellent staff at front desk and Lori who serves breakfast is wonderful " [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Hampton Inn Brattleboro](//images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Staff was very helpful " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Travelodge by Wyndham Brattleboro VT](//images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/19b6c01d_y.jpg) ### Travelodge by Wyndham Brattleboro VT 6/10 Okay "For the money during peep season it was ok. Otherwise it’s a low quality stay" [](https://expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) ![The Covered Bridge Inn](//images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg) ### The Covered Bridge Inn 10/10 Excellent "We were initially put off by the look of the outside of this “Inn”! But it turns out we were greeted by a smiling and polite person during check in. The room was large, clean, and comfortable. The bathroom had thick towels and well stocked. All and all it was a very pleasant stay at a very reasonable price!" [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "Such a unique and fun place, beautifully crafted, tastefully decorated. I wish we could stay a week!" [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ## Find out more about Chesterfield ## Chesterfield Vacation Homes information | Number of reviews | 162 | | --- | --- | | Accommodation | 149 Vacation Homes | | Lowest Price | CA $282 | | Highest Price | CA $1,020 | ## 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) - 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