Title: Chester Cottages from CA $414 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d183058.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d183058.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d183058.Travel-Guide-Flights)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d183058.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d183058.Destination-Travel-Guides) ![Connecticut River Autumn Landscape with the view of landmark architectures on the woodland hill, a tranquil New England scenery](https://images.trvl-media.com/place/183058/c14a28ee-62e4-4e76-85a4-650e5a230000.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chester Cottage Rentals from CA $414 - ![](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 [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester cottages ![Exterior](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/65eed284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/3067f697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom cottage with Grove Beach 🏖️ access. [](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) Clinton 9.2/10 Wonderful (36) "Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle CA $99 CA $248 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c0b20841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/41a9fc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c5a2aa07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/ec09d195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk [](https://www.expedia.ca/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) Waterford 10/10 Exceptional (14) "The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jorie M. CA $186 CA $414 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83490000/83488400/83488389/039094e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/84000000/83490000/83488400/83488389/b9218042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83490000/83488400/83488389/57d1eb2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/84000000/83490000/83488400/83488389/cbcd8d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 115 Rose Cottage with 2 bedroom walk to Groton Bay [](https://www.expedia.ca/Groton-Hotels-115-Rose-Cottage-With-2-Bedroom-Walk-To-Groton-Bay.h83488389.Hotel-Information) Groton 8.8/10 Excellent (8) "Very nice little place. Quite, clean and only minutes from Mystic and downtown New London." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas C. CA $138 CA $446 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Groton-Hotels-115-Rose-Cottage-With-2-Bedroom-Walk-To-Groton-Bay.h83488389.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/b8b9f031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/f4b0f948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/07929bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/d94ed7d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tiny Cottage at Clem & Clyde's [](https://www.expedia.ca/Montville-Hotels-The-Tiny-Cottage-At-Clem-Clydes.h122919838.Hotel-Information) Oakdale, 10/10 Exceptional (1) "This is a perfect place to get away from the city and feel nostalgic about the memories I had when I lived in a small village. It’s a cozy, warm little cottage—perfect for staying a few days. The setup and furniture in the house have everything we need, even for just a one-night stay. The room is clean and spotless, and very well maintained. The host, Tom, is very friendly and helped introduce us to his animals. We arrived during the first snowfall of the winter season, and the view outside the... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Junlin CA $118 CA $163 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Montville-Hotels-The-Tiny-Cottage-At-Clem-Clydes.h122919838.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/71856d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/a3e46cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) Old Saybrook Center 9.6/10 Exceptional (39) "Great property, would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) charles b. CA $339 CA $700 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.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=2025-12-28&endDate=2025-12-29®ionId=183058&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Villas [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America®ionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VILLA) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America®ionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America®ionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America®ionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America®ionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CONDO) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Connecticut%2C+United+States+of+America®ionId=183058&latLong=41.402206%2C-72.482498&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CABIN) ![](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%2FChester-Cottages.d183058-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d183058-aaCottages.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Hyatt Place Uncasville - Casino Area](https://images.trvl-media.com/lodging/3000000/2600000/2593900/2593874/46d6d7fc_y.jpg) ### Hyatt Place Uncasville - Casino Area 10/10 Excellent "Very nice place. The only grip we have Is the sink should be in the bathroom." [](https://expedia.ca/Montville-Hotels-Hyatt-Place-Mohegan-Sun.h2593874.Hotel-Information) ![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg) ### Motel 6 New Haven - Branford, CT 10/10 Excellent "Clean room" [](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information) ![Best Western Plus New England Inn & Suites](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/ff6d89d5_y.jpg) ### Best Western Plus New England Inn & Suites 10/10 Excellent "Ok" [](https://expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.Hotel-Information) ![Mohegan Sun](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3_y.jpg) ### Mohegan Sun 10/10 Excellent "Yes" [](https://expedia.ca/Montville-Hotels-Mohegan-Sun.h894248.Hotel-Information) ![Microtel Inn & Suites by Wyndham Uncasville Casino Area](https://images.trvl-media.com/lodging/1000000/810000/801800/801773/ed4520c7_y.jpg) ### Microtel Inn & Suites by Wyndham Uncasville Casino Area 10/10 Excellent "Small but very clean room, extremely pleasant front desk staff, simple breakfast with 24 hour coffee, and more than adequate parking. The price was definitely right, and I would stay here again if passing through. Note… There’s a fridge in the room, but no microwave. You can use the microwave in the lobby." [](https://expedia.ca/Montville-Hotels-Microtel-Inn-Suites-By-Wyndham-Uncasville.h801773.Hotel-Information) ![Best Western Niantic - New London/Mystic Area](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w3834h2560x6y0-25f93ce9_y.jpg) ### Best Western Niantic - New London/Mystic Area 10/10 Excellent "Clean, quiet, and staff was super professional. " [](https://expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![Hampton Inn Norwich](https://images.trvl-media.com/lodging/19000000/18260000/18258300/18258245/d98f34e1_y.jpg) ### Hampton Inn Norwich 10/10 Excellent "We stay here whenever we go to Mohegan Sun. The front desk is always very friendly and helpful. Breakfast is terrific. I was pleasantly surprised." [](https://expedia.ca/Norwich-Hotels-Hampton-Inn-Norwich.h18258245.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "My stay with Saybrook Point Resort & Marina was amazing. Clean room, amazing staff and amenities! I plan to return again!" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Sleep Inn & Suites Niantic North](https://images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a_y.jpg) ### Sleep Inn & Suites Niantic North 10/10 Excellent "Very clean room Did not have the breakfast as we left prior to it starting. Would stay there again " [](https://expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) ## Find out more about Chester ## Chester Cottages information | Number of reviews | 61 | | ----------------- | ------------ | | Accommodation | 130 Cottages | | Lowest Price | CA $414 | | Highest Price | CA $700 | ## Frequently asked questions ### How much do cottages in Chester cost? ### How many cottages are there in Chester? ### Why book your cottage in Chester with Expedia? ### How can I find cheap cottages in Chester? ### What is there to do in Chester near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Chester Center ](https://www.expedia.ca/4Star-Chester-Center-Chester-Hotels.s40-n553248635976479536-0.Travel-Guide-Filter-Hotels) - [Hotels near Chamard Vineyards ](https://www.expedia.ca/Chamard-Vineyards-Hotels.0-l6309929-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Chester Center ](https://www.expedia.ca/Chester-Center-Chester-Hotels-Historic-Hotel.0-n553248635976479536-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - 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