Title: Book the Best ROMANTIC Hotels in Chester, CT - Chester Romantic Getaways | 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) ![](https://mediaim.expedia.com/destination/2/c5d2a9a368de96fc49a7ea71252ca638.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Annette Babek # Find Romantic Hotels in Chester, CT ![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 availability on Chester Romantic Hotels Tonight [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-09-30&endDate=2025-10-01&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-10-01&endDate=2025-10-02&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-10-03&endDate=2025-10-05&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Romantic Hotels ![Interior](https://images.trvl-media.com/lodging/19000000/18990000/18980200/18980197/00575e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18990000/18980200/18980197/76ac236b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18990000/18980200/18980197/4ca5a514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/19000000/18990000/18980200/18980197/52a6489d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Artisan Waterfall Escape \[Walk to Downtown\] Chester Center 10/10 Exceptional (44) "Excellent location. Really interesting construction. Worth staying just to explore the house." [](https://www.expedia.ca/Chester-Hotels-Stunning-Artisan-Waterfall-Escape-Walk-To-Downtown.h18980197.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=2025-10-14&endDate=2025-10-15®ionId=183058&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area](//images.trvl-media.com/lodging/1000000/810000/800500/800485/75539c58_y.jpg) ### Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area 10/10 Excellent "Amazing customer service! Everything clean and spacious. " [](https://expedia.ca/Montville-Hotels-Fairfield-By-Marriott-Inn-Suites-Uncasville-Groton-Area.h800485.Hotel-Information) ![Inn at Middletown](//images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540_y.jpg) ### Inn at Middletown 10/10 Excellent "Wonderful hotel...newly renovated. Great breakfast at the Tavern, dinner would have been great too. Room was very spacious and beds comfortable. Really liked the decore sort of modern colonial. Fresh cookies at the desk and got to grab a glass of wine from the bar to take to the room. Staff was extremely friendly and helpful. Id stay again if ever in Middletown!" [](https://expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.Hotel-Information) ![Hyatt Place Uncasville - Casino Area](//images.trvl-media.com/lodging/3000000/2600000/2593900/2593874/46d6d7fc_y.jpg) ### Hyatt Place Uncasville - Casino Area 10/10 Excellent "Friendly staff. Hotel was very clean. Breakfast was hot and delicious " [](https://expedia.ca/Montville-Hotels-Hyatt-Place-Mohegan-Sun.h2593874.Hotel-Information) ![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Loved everything about this property. Location, Staff, Amenities. Decor and furniture beautiful. " [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Sleep Inn & Suites Niantic](//images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a_y.jpg) ### Sleep Inn & Suites Niantic 10/10 Excellent "Great staff. The front desk man quickly changed our room when my husband noted it would benoisy, being by the elevator and ice machine. He's a light sleeper, especially bothered by noise. The breakfast room attendent was the most attentive I've ever seen. Kept the eggs and sausages coming, piping hot, and wiped down the tables immediately. " [](https://expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) ![Mohegan Sun](//images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3_y.jpg) ### Mohegan Sun 10/10 Excellent "We went to get away from all the stress and was exactly what we got. The room was beautiful. We unexpectedly were upgraded to a suite and took advantage of the what the room offered. Ate at great places, experienced a WNBA game for the first time. Everyone on staff was so friendly making us feel right at home. We have always had a great experience when going to Mohegan in the past but this time was so much more appreciated. " [](https://expedia.ca/Montville-Hotels-Mohegan-Sun.h894248.Hotel-Information) ![Microtel Inn & Suites by Wyndham Uncasville Casino Area](//images.trvl-media.com/lodging/1000000/810000/801800/801773/ed4520c7_y.jpg) ### Microtel Inn & Suites by Wyndham Uncasville Casino Area 10/10 Excellent "-" [](https://expedia.ca/Montville-Hotels-Microtel-Inn-Suites-By-Wyndham-Uncasville.h801773.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Chester? > If you and your partner need a romantic vacation, we've got just the ticket. If you'd like to explore some of the area's notable sights, you might make a stop by Connecticut River, Norma Terris Theater, or Connecticut Valley Railroad State Park Trail. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Chester? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chester: 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. Average annual precipitation for Chester is 54 inches. ### What is there to do in Chester? > There's nothing better than seeing a new destination with your sweetheart, so consider checking out all that Chester has to offer. Connecticut River, Norma Terris Theater, and Connecticut Valley Railroad State Park Trail are worth a stop when you're out and about. ### What's the best way to get to Chester and around town during my romantic getaway? > This information about transportation options in Chester might help your romantic trip get off to a smooth start: Make your way to Chester with a flight to New Haven, CT (HVN-Tweed - New Haven Regional), which is the closest major airport located 23.1 mi (37.2 km) from the city center. 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