Title: Chesterfield Condo Rentals | 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 Condos Rentals in Chesterfield ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6052872&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chesterfield Condo Rentals ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33490000/33482500/33482423/324fe2d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33490000/33482500/33482423/5d0ca595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33490000/33482500/33482423/907c62fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/34000000/33490000/33482500/33482423/c90a06a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-in/Ski-out Condo with central air -Seasons on Mt. Snow West Dover 9.8/10 Exceptional (96) "It is so clean and well maintained. It is ski in ski out. Would stay again in a minute " [](https://www.expedia.ca/West-Dover-Hotels-True-Ski-InSki-Out-Condo.h33482423.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076095/a80d861b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076095/5c368338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076095/8797e1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076095/e5818cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-story mountain condo with deck, balcony, shuttle to slopes, fireplace, & W/D Dover 10/10 Exceptional (3) "This condo was clean and very beautiful." [](https://www.expedia.ca/West-Dover-Hotels-3-Story-Mountain-Condo-With-Deck.h91076095.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109140000/109134500/109134411/db473738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109140000/109134500/109134411/dcb4cff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109140000/109134500/109134411/9897078f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109140000/109134500/109134411/a5ff8b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy condo w/ wood-burning fireplace, deck, wifi, w/d, bus route, TVs, cable Dover [](https://www.expedia.ca/West-Dover-Hotels-Cozy-Condo-W-Wood-Burning-Fireplace.h109134411.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100980000/100977300/100977273/a0b1b96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100980000/100977300/100977273/0b61fd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100980000/100977300/100977273/0f4c4e35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100980000/100977300/100977273/f87c3d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint 2 bedroom condo with Loft in Southern Vermont min. from hiking and golf Dover 9.0/10 Wonderful (2) "Place was nice and clean, everything was provided. We had one little hiccup with the hot water, but that was corrected fast by the property manager. Everything else was great." [](https://www.expedia.ca/West-Dover-Hotels-Quaint-3-Bedroom-Condo-At-Dover-Green-Minutes-From-Mount-Snow.h100977273.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116490000/116481100/116481090/ec3f0cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116490000/116481100/116481090/0a39af36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi](https://images.trvl-media.com/lodging/117000000/116490000/116481100/116481090/e96864db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116490000/116481100/116481090/923c7b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom condo in awesome Brattleboro with WiFi, AC Brattleboro [](https://www.expedia.ca/Brattleboro-Hotels-Charming-2-Bedroom-Condo-In-Awesome-Brattleboro-With-WiFi.h116481090.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/80000000/79710000/79704800/79704765/73f3772d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/80000000/79710000/79704800/79704765/f903fbb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/80000000/79710000/79704800/79704765/6445fd62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/80000000/79710000/79704800/79704765/c9cdadbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Condo on Mount Snow access Road Sleeps 12 west dover [](https://www.expedia.ca/West-Dover-Hotels-Luxury-Condo-On-Mount-Snow-Access-Road-Sleeps-12.h79704765.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=2025-10-11&endDate=2025-10-12®ionId=6052872&adults=2&lodging=CONDO&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-Condos.d6052872-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Condos.d6052872-aaCondos.Travel-Guide-Accommodation) ## Top Chesterfield Hotel Reviews ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "It was spectacular! Restful, peaceful, wonderful!!! Everything you need in a little kitchen area. Cute shops and restaurants in nearby towns. Very nice fire pit, Hiking trails right on property. Adorable sheep (don’t worry- no smell) The owners were amazing. I hope I get to stay again sometime. " [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.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 "Clean and quiet" [](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 "It was just an overnight stay. The room was very clean, the staff were helpful with questions. I will definitely book again." [](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 "It was quiet and the staff was friendly. Great and easy to get to location." [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Very cute vintage stay, prompt communicative staff. Walkable to a very cute bookstore, coffee, breakfast spots and a vegan restaurant (vegan AF) that was 10/10. Beautiful view and accessible parking. " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Black Mountain Inn](//images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c_y.jpg) ### Black Mountain Inn 10/10 Excellent "Excellent staff!" [](https://expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![The Putney Inn](//images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "The room was clean, even if a bit dated looking. The staff were great!" [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Riverside Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg) ### Riverside Hotel, an Ascend Collection Hotel 10/10 Excellent "Cleaning is excellent " [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Days Inn by Wyndham Keene NH](//images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg) ### Days Inn by Wyndham Keene NH 10/10 Excellent "A group of us come here every year and we never hesitate to come back. Not the Ritz, but perfectly fine and very reasonably priced to have access to a pretty nice part of NH." [](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ## Find out more about Chesterfield ## Chesterfield Condo Rentals information | Number of reviews | 98 | | --- | --- | | Accommodation | 10 Condo Rentals | | Lowest Price | | | Highest Price | | ## 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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