Title: Book the Best Chester, CT ALL INCLUSIVE Resorts and Hotels | 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) ![Enjoying a #weekend out in #Connecticut #Marina #River #Autumn](https://images.trvl-media.com/place/6004513/c0f041d5-f895-44ec-b954-f8bc1e935e1c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Erick # Find All Inclusive Resorts and Hotels in Chester, CT - ![](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 availability on Chester All Inclusive Resorts and Hotels Tonight [Nov 12 - Nov 13](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-12&endDate=2025-11-13&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 13 - Nov 14](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-13&endDate=2025-11-14&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester All Inclusive Resorts and Hotels ## Top Chester Hotel Reviews ## Frequently asked questions ### Looking for Chester all-inclusive resorts? > Chester offers a host of things to see and do such as Connecticut River and Norma Terris Theater. View our all-inclusive accommodations where you can enjoy a host of amenities such as entertainment, kid's clubs, and of course food and beverages all included in the price. Many of our all-inclusive resorts also feature activities such as golf, yoga, water sports, and more, which you can enjoy without any additional cost. ### What is there to do near my all-inclusive resort in Chester? > If you want to explore the area around your all-inclusive resort, visit Connecticut River and Norma Terris Theater and see why travelers like Chester! Other attractions include Connecticut Valley Railroad State Park Trail, Chester Creek Marina, and Gillette Castle State Park. ### When's the best time for an all-inclusive stay in Chester? > There's nothing like an all-inclusive vacation in Chester to rejuvenate you, especially when you know what kind of weather to expect. Here's some info to help you choose when to book: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 35°F. 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