Title: Book the Best Middletown WINERY Hotels in 2026 | 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 # Find Winery Hotels in Middletown, CT from CA $188 - ![](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 Winery Hotels Tonight [Jan 5 - Jan 6](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-01-05&endDate=2026-01-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-01-06&endDate=2026-01-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8862&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown hotels with winery ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/321be2b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/0a69331b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/ee5526e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103030000/103030000/103029991/a34edd2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All New Studio apartment in center of town [](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information) Wallingford Center 10/10 Exceptional (2) "I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nadine C. CA $158 CA $396 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Wallingford-Hotels-All-New-Studio-Apartment-In-Center-Of-Town.h103029991.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/0888acaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/bdac0629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/2db3f072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/646c7316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All New 1BR with tons of Charm [](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information) Wallingford Center 9.8/10 Exceptional (7) "Charming, unique, and very comfortable. Would surely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David S. CA $158 CA $396 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/5dc7d6d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/27e9804b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/dca364d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/1cbdfdde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Hartford Avon [](https://www.expedia.ca/Hartford-Hotels-Residence-Inn-By-Marriott-Hartford-Avon.h1074390.Hotel-Information) Avon 8.8/10 Excellent (420) "The staff is amazing friendly and always there for advice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $174 CA $200 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Hartford-Hotels-Residence-Inn-By-Marriott-Hartford-Avon.h1074390.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a31fd902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a34caa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/89e5a275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/8613ee04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins! [](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information) Clinton 10/10 Exceptional (3) "Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elya D. CA $192 CA $729 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/7edf3766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/w3997h2667x0y0-8dc04f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/1d0ef914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/2dfa38e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard New Haven Wallingford [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-New-Haven-Wallingford.h19783.Hotel-Information) Wallingford 8.8/10 Excellent (787) "Clean room, friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $174 CA $201 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-New-Haven-Wallingford.h19783.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273388/e8764690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273388/90dd1f9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273388/7923d4f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![37-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273388/6cc530a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Wallingford-Meriden [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Wallingford-Meriden.h1273388.Hotel-Information) Wallingford 9.0/10 Wonderful (910) "Staff was very friendly and helpful stay was overall very pleasant!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela CA $164 CA $188 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Wallingford-Meriden.h1273388.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/fb2335a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 Bedroom, Non Smoking (Room 211)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/89c2227e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 Bedroom, Non Smoking (Room 322)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/94ca860b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copper Beech Inn [](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information) Ivoryton 8.6/10 Excellent (506) "Very nice property. Very clean. Staff was very nice - very good breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marilyn CA $383 CA $441 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/1bc1a012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/cd7d0c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/w1026h680x0y3-1207c37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/010bda9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville [](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.Hotel-Information) Collinsville 10/10 Exceptional (61) "Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanmarie G. CA $290 CA $538 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w905h683x60y0-7e221032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/39eb1814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w905h683x59y0-8f890c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821015/w904h683x60y0-a0d1107c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Overlook - Check the view from your deck! [](https://www.expedia.ca/Canton-Hotels-River-Overlook.h90821015.Hotel-Information) Collinsville 10/10 Exceptional (23) "The place was perfect for the two of us. It was close to both our kids homes." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tomas M. CA $184 CA $367 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Canton-Hotels-River-Overlook.h90821015.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/f8cef332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h960x0y0-cce9554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h954x0y0-9b5015ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h953x0y0-69414cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard [](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information) Saybrook Manor 9.6/10 Exceptional (133) "We loved our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deana L. CA $343 CA $794 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.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=2026-01-19&endDate=2026-01-20®ionId=8862&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Middletown Hotel Reviews ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "Clean comfortable room, friendly staff, great breakfast" [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "Great place." [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Inn at Middletown](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540_y.jpg) ### Inn at Middletown 10/10 Excellent "everything was great " [](https://expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Great place!" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Red Roof Inn Meriden](https://images.trvl-media.com/lodging/1000000/10000/2900/2831/05873179_y.jpg) ### Red Roof Inn Meriden 10/10 Excellent "Great place, clean, cool people" [](https://expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.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 "Great experience and staff" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg) ### Hampton Inn & Suites Hartford/Farmington 10/10 Excellent "It was great, clean, friendly!!" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.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 "Yes" [](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.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 "Awesome place " [](https://expedia.ca/Hartford-Hotels-Hilton-Hartford.h1637.Hotel-Information) ## Frequently asked questions ### How much does a winery hotel in Middletown cost? ### Which area of Middletown is best to stay in for vineyards and wineries? > For couples seeking a romantic escape, the nearby town of Haddam offers a quaint atmosphere, complete with beautiful views of the river and historic sites. You might enjoy a picnic at the stunning scenery of the Powder Ridge Park or take a sunset stroll along the river, making it an idyllic setting for creating cherished memories together. > > > Families will appreciate the educational opportunities that come with vineyard visits, as many wineries offer tours that explain the wine-making process. The area's family-friendly attractions, like the nearby Dinosaur State Park and the Kidcity Children's Museum, ensure that there's something for everyone, combining fun with learning. ### What winery activities should we do in Middletown? > For couples seeking a romantic outing, consider a guided vineyard tour followed by a private tasting. Many wineries offer intimate experiences, allowing you to savour the nuances of their wines while learning about the winemaking process. The serene atmosphere, coupled with stunning vistas, creates a superb backdrop for a memorable day together. > > > Families can also enjoy the winery experience in Middletown. Several local vineyards host family-friendly events, including grape stomping during harvest season or picnics on the lawn. Engaging educational tours ensure that younger visitors learn about viticulture in a fun and interactive way, making it a delightful outing for everyone. > > > If you're looking to enhance your visit, pair your wine-tasting adventure with a culinary experience. Many wineries offer farm-to-table dining options or food pairings that complement their wines, providing a feast for both your palate and your senses. ### Does Middletown host any wine festivals or events? > For couples seeking a romantic outing, attending a wine festival in Middletown can be a wonderful way to spend time together. Imagine strolling hand in hand through rows of tasting tents, sampling exquisite wines while enjoying live music and delicious food pairings. The intimate atmosphere of these events provides a ideal setting for connection and conversation. > > > Families can also find joy in these wine events, especially those that include activities for children. Some festivals feature family-friendly options, such as craft booths, games, and outdoor activities, allowing parents to relax with a glass in hand while the kids enjoy supervised fun. > > > Whether you're a wine aficionado or simply looking for a memorable experience, Middletown's wine festivals present a fantastic opportunity to explore local flavours and enjoy the community spirit. ### How can I save on a winery hotel in Middletown with Expedia? ### Is it cheaper to book flights and a winery hotel in Middletown as a package deal? ### Can I cancel my winery 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) - 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