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Find Romantic Hotels in Middletown, CT

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Check availability on Middletown Romantic Hotels

Our top choices for Middletown romantic hotels

Front of property - evening/night
Inn at Middletown

Inn at Middletown

3.5 star property
Washington Street Historic District
9.0 out of 10, Wonderful, (538)
"Clean room, friendly staff. "
United States
Katharine
Inn at Middletown
Lobby sitting area
New Haven Hotel

New Haven Hotel

3.5 star property
Downtown New Haven
9.0 out of 10, Wonderful, (1921)
"Very nice hotel. "
United States
REINA
The price is AED 434
AED 499 total
includes taxes & fees
18 Dec - 19 Dec
New Haven Hotel
Lobby
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3.0 star property
Waterbury
8.4 out of 10, Very Good, (1062)
"Everything was great 👍 "
United States
Janet
The price is AED 327
AED 376 total
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Waterbury Downtown
Exterior
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3.0 star property
Southington
8.2 out of 10, Very Good, (1002)
"Highly recommend staying here. The rooms are clean and the staff go above and beyond to make sure that guests have a comfortable stay."
United States
Veronica
The price is AED 334
AED 384 total
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn Cheshire - Southington by IHG
Courtyard
Sheraton Hartford South Hotel

Sheraton Hartford South Hotel

3.5 star property
Rocky Hill
8.4 out of 10, Very Good, (1001)
"Very clean room, inviting lobby, and very nice employees at check in and checkout "
United States
Caroline
The price is AED 371
AED 427 total
includes taxes & fees
2 Jan - 3 January 2026
Sheraton Hartford South Hotel
Interior
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 star property
Avon
8.4 out of 10, Very Good, (1005)
"Very nice place to stay"
United States
Alvero
The price is AED 364
AED 498 total
includes taxes & fees
28 Dec - 29 Dec
Avon Old Farms Hotel
BBQ/picnic area
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3.0 star property
Farmington
8.4 out of 10, Very Good, (1003)
"Check-in was easy and the front desk person was friendly. The room is clean and well stocked with everything we need."
United States
Catherine
The price is AED 400
AED 460 total
includes taxes & fees
4 Jan - 5 January 2026
Homewood Suites by Hilton Hartford-Farmington
Lobby sitting area
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3.0 star property
Windsor
9.0 out of 10, Wonderful, (1005)
"Amazing stay "
United States
Amber
The price is AED 443
AED 509 total
includes taxes & fees
1 Jan - 2 January 2026
HYATT house Hartford North/Windsor
Exterior
Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden

3.0 star property
Wallingford
8.8 out of 10, Excellent, (999)
"Surprisingly beautiful hotel! "
United States
Lisa
The price is AED 436
AED 501 total
includes taxes & fees
4 Jan - 5 January 2026
Hilton Garden Inn Wallingford/Meriden
Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (339)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is AED 888
AED 1,022 total
includes taxes & fees
1 Jan - 2 January 2026
Madison Beach Hotel
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.
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Top Middletown Hotel Reviews

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"Everything was great 👍 "
Janet 3-night trip
Posted 1 day ago
Courtyard by Marriott Waterbury Downtown

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Frequently asked questions

Searching for romantic hotels in Middletown?
Are you and your partner looking for a romantic escape? If you want to explore the area, you might head to Wadsworth Mansion, Connecticut River, or Kidcity Children's Museum. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity 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 Middletown?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Middletown: 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 33°F. Average annual precipitation for Middletown is 53 inches.
What is there to do in Middletown?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Middletown. You might think about visiting Wadsworth Mansion, Connecticut River, or Kidcity Children's Museum.
What's the best way to get to Middletown and around town during my romantic getaway?
This information about transportation options in Middletown might help your romantic getaway go off without a hitch: Make your way to Middletown with a flight to New Haven, CT (HVN-Tweed - New Haven Regional), which is the closest major airport located 23.8 mi (38.2 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.