Title: Book the Best ROMANTIC Hotels in Chester, CT from CA $150 - 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 from CA $150 - ![](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 Romantic Hotels Tonight [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Chester Romantic Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1500/1450/d9b5e4b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1500/1450/deb4c94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1500/1450/2413bff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1500/1450/76c1f8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Norwich by IHG Westside Norwich 7.6/10 Good (1001) "It's a very nice and friendly place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lillian CA $131 CA $150 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Norwich-Hotels-Holiday-Inn-Norwich.h1450.Hotel-Information) ![Casino](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/2c209688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![19 restaurants, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/d7f63730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/3c373018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mohegan Sun Montville 9.2/10 Wonderful (2078) "Convenient location and plenty of parking. Great dining options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenny CA $233 CA $303 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Montville-Hotels-Mohegan-Sun.h894248.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/aeb3a957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/dc0e4dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/1095c0dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/2000000/1510000/1506700/1506634/08b482c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Harbor Hill Marina Niantic 9.4/10 Exceptional (1002) "Clean great staff great breakfast quiet guests beautiful scenery 10/10" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Trey CA $223 CA $256 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Niantic-Hotels-Inn-At-Harbor-Hill-Marina.h1506634.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/8300/8221/f54b808b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/8300/8221/bf453fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/8300/8221/ac81a89c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/1000000/10000/8300/8221/fe5d083b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Hartford South Hotel Rocky Hill 8.4/10 Very good (1005) "Great location and convenient for our travels up north on our way to Maine." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roger CA $155 CA $178 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Hartford-Hotels-Sheraton-Hartford-South-Hotel.h8221.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/625fce42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ef9d54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/b8f87b0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Beach Hotel Madison Center 9.4/10 Exceptional (327) "Great stay!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $344 CA $395 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/8d6a4015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/8a31f79b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/19bd6a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/ad096b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Wallingford/Meriden Wallingford 9.0/10 Wonderful (1002) "Beautiful Hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon CA $172 CA $198 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-WallingfordMeriden.h11440147.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/1f9e04f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/8c361790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/eff2fea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Middletown Middletown 9.0/10 Wonderful (521) "Very nice property convenient to Wesleyan and Middletown" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deb [](https://www.expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/15200/15113/44902ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/15200/15113/e210c0b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/15200/15113/d178bb52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15200/15113/5436b0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Branford/New Haven Branford 6.6/10 (1001) "It's was good place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Evette CA $139 CA $160 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/New-Haven-Hotels-Baymont-By-Wyndham-BranfordNew-Haven.h15113.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/46915263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/865dda17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Clinton Room](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/6c9c9c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/36000000/35600000/35596400/35596310/f2c9a8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westbrook Inn B&B Westbrook Center 9.8/10 Exceptional (173) "Beautiful place and wonderful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $296 CA $329 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Old-Saybrook-Hotels-Westbrook-Inn-Bed-And-Breakfast.h35596310.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/65651fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/770255ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/f7da52a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saybrook Point Resort & Marina Old Saybrook Center 9.4/10 Exceptional (1008) "Beautiful property, we loved our room, friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Natalie CA $334 CA $419 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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=2025-11-18&endDate=2025-11-19®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 "This place is great. So close to Mohegan sun u can walk if needed. Staff was so friendly " [](https://expedia.ca/Montville-Hotels-Fairfield-By-Marriott-Inn-Suites-Uncasville-Groton-Area.h800485.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 "This hotel has everything!!! We went for a girls’ night away, and we never had to leave. The heated pools and steam/sauna rooms were wonderful. The on-site restaurants and room service options were delicious. Our room was very clean and cozy, especially with the service of a staff member starting a fire for us in the fireplace. Every single staff member was incredibly helpful, friendly and hospitable, making the entire stay 5 stars! " [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![The Spa at Norwich Inn](//images.trvl-media.com/lodging/1000000/10000/400/330/4d5b6bcc_y.jpg) ### The Spa at Norwich Inn 10/10 Excellent "The spa was wonderful! My friend and I had facials massages and foot massages and they were perfect! The people working at the Norwich Inn are so friendly and helpful. The best part is that you can hang out in your robe and enjoy the spa facilities all day! We absolutely loved it and didn’t want to leave … we already booked a return trip for June!" [](https://expedia.ca/Norwich-Hotels-The-Spa-At-Norwich-Inn.h330.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 "Great room!" [](https://expedia.ca/Montville-Hotels-Hyatt-Place-Mohegan-Sun.h2593874.Hotel-Information) ![Mohegan Sun](//images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3_y.jpg) ### Mohegan Sun 10/10 Excellent "The hotel room. Was nice and quiet Never had any issues with the stay. " [](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 "We love it " [](https://expedia.ca/Montville-Hotels-Microtel-Inn-Suites-By-Wyndham-Uncasville.h801773.Hotel-Information) ![Regency Inn & Suites New London, Mystic](//images.trvl-media.com/lodging/1000000/10000/6400/6341/fbddb1be_y.jpg) ### Regency Inn & Suites New London, Mystic 10/10 Excellent "My room was exceptionally clean and staff was kind and friendly." [](https://expedia.ca/New-London-Hotels-Regency-Inn-And-Suites-New-London.h6341.Hotel-Information) ![Inn at Middletown](//images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540_y.jpg) ### Inn at Middletown 10/10 Excellent "Clean room, friendly staff. " [](https://expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.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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