Title: Book the Best Middletown LUXURY Hotels - Upscale Hotels in Middletown, CT | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d8862.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d8862.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.ca/Cheap-Flights-To-Middletown.d8862.Travel-Guide-Flights)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d8862.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d8862.Destination-Travel-Guides) ![This photo was taken during a nice fall weekend. The water level was low enough to cross to the other side to capture the falls from a different angle than most. Best time however is early morning before most people get there.](https://images.trvl-media.com/place/8862/b3bca6a9-4805-449f-b3d1-dba87c1e3a0f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Simmie Reagor ![](https://images.trvl-media.com/place/8862/b3bca6a9-4805-449f-b3d1-dba87c1e3a0f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Middletown Luxury Hotels Tonight [Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-01-27&endDate=2026-01-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-01-28&endDate=2026-01-29&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-01-30&endDate=2026-02-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Middletown Hotel Reviews ![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "Very clean room. " [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![The Capitol Hotel](https://images.trvl-media.com/lodging/1000000/10000/6800/6777/2c26b973_y.jpg) ### The Capitol Hotel 10/10 Excellent "The hotel stay was perfect. The room was clean and comfortable. Location was perfect - we needed to be near the convention center and we were just 5 minutes away. Would stay here again." [](https://expedia.ca/Hartford-Hotels-The-Capitol-Hotel.h6777.Hotel-Information) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "Excellent room and courteous welcome." [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "I have stayed here a number of times, and each time the room has been spotless and smells fresh. The staff is very friendly and always offers to help in some way, whether it's to get the snow off my car or provide bottled water. I will be staying here again!" [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Hampton Inn & Suites Hartford/East Hartford](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5_y.jpg) ### Hampton Inn & Suites Hartford/East Hartford 10/10 Excellent "Dana the front desk associate was sooo nice and helpful! " [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Nice Room - Overlooks Yale’s campus. " [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![DoubleTree by Hilton Hartford Downtown](https://images.trvl-media.com/lodging/1000000/10000/1700/1637/1dfc2c6d_y.jpg) ### DoubleTree by Hilton Hartford Downtown 10/10 Excellent "Good" [](https://expedia.ca/Hartford-Hotels-Hilton-Hartford.h1637.Hotel-Information) ## Frequently asked questions ### Which area of Middletown is best to stay in for luxury hotels? > This area is the heart of Middletown, known for its historic architecture and a wide selection of dining options. Main Street itself is a long, bustling thoroughfare lined with restaurants, independent shops, and cultural venues like the Oddfellows Playhouse. It's a very walkable area, stretching roughly from the Wesleyan University campus in the south to the Connecticut River waterfront in the north. > > > Couples looking for a sophisticated getaway will find downtown Middletown an excellent fit. They can enjoy evenings dining at upscale restaurants, catching a show, or exploring the unique boutiques. The proximity to the Connecticut River also offers opportunities for scenic strolls along the water. > > > For solo travellers, downtown provides a lively yet manageable environment. They can easily access a variety of eateries, coffee shops, and cultural activities without needing a car. ### How much does a luxury hotel in Middletown cost? ### What luxury activities and experiences are there in Middletown? > This central part of Middletown is where you'll find a concentration of upscale dining, unique boutiques, and access to the Connecticut River. Main Street itself is a well-maintained thoroughfare with historic buildings, and it's very walkable, making it easy to explore the high-end offerings. > > > For couples looking for a sophisticated getaway, this area is perfect. You can enjoy fine dining at restaurants focusing on local and seasonal ingredients, often with extensive wine lists. After dinner, there are several establishments offering craft cocktails or live music in an elegant setting. Many of the boutique shops here feature artisan goods, bespoke clothing, and unique home decor, providing opportunities for special purchases. > > > Travellers seeking a relaxing and indulgent experience will appreciate the proximity to wellness facilities. Some hotels in this area offer high-end fitness equipment, spa services, or even heated indoor pools, allowing for a complete rejuvenation. ### How can I save on a luxury hotel in Middletown with Expedia? ### Is it cheaper to book a luxury Middletown hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Cars - More ways to book - [4 Star Hotels in Durham ](https://www.expedia.ca/4Star-Durham-Hotels.s40-0-d6004516.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Berlin ](https://www.expedia.ca/5Star-Berlin-Hotels.s50-0-d55586.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Cobalt ](https://www.expedia.ca/5Star-Cobalt-Hotels.s50-0-d3000429981.Travel-Guide-Filter-Hotels) - [Aparthotels in Berlin ](https://www.expedia.ca/Berlin-Apart-Hotels.d55586-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Berlin ](https://www.expedia.ca/Berlin-Bed-And-Breakfast.d55586-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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