Photo by Simmie Reagor

Find Romantic Hotels in Middletown, CT

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Middletown Romantic Hotels

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top 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, (537)
"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, (1913)
"Great check in and comfortable room."
United States
Kathryn
The price is SAR 310
SAR 357 total
includes taxes & fees
8 Dec - 9 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, (1064)
"This is my second time, and I think I will be coming more often."
United States
Linda
The price is SAR 284
SAR 326 total
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Waterbury Downtown
Interior
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 star property
Avon
8.4 out of 10, Very Good, (1010)
"Very nice place to stay"
United States
Alvero
The price is SAR 447
SAR 596 total
includes taxes & fees
3 Dec - 4 Dec
Avon Old Farms Hotel
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1008)
"We love the stay everything was perfect"
United States
angelica
The price is SAR 595
SAR 749 total
includes taxes & fees
3 Dec - 4 Dec
Water's Edge Resort & Spa
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (175)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is SAR 565
SAR 628 total
includes taxes & fees
8 Dec - 9 Dec
Westbrook Inn B&B
Breakfast and brunch served
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4.0 star property
Downtown New Haven
8.4 out of 10, Very Good, (1029)
"Very friendly staff"
United States
Tammy
The price is SAR 567
SAR 653 total
includes taxes & fees
3 Dec - 4 Dec
Omni New Haven Hotel at Yale
Exterior
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3.0 star property
Southington
8.4 out of 10, Very Good, (1016)
"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 SAR 417
SAR 480 total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Cheshire - Southington by IHG
Lobby sitting area
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3.0 star property
Windsor
9.0 out of 10, Wonderful, (1012)
"Amazing stay "
United States
Amber
The price is SAR 459
SAR 528 total
includes taxes & fees
1 Jan - 2 January 2026
HYATT house Hartford North/Windsor
Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (338)
"Staff and hotel are lovely "
United States
Steven
The price is SAR 920
SAR 1,058 total
includes taxes & fees
8 Dec - 9 Dec
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Top Middletown Hotel Reviews

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"They were amazing!! Everyone was so kind and professional. I had to extend my stay due to I foreseen negative reasons and they made it easy and asked if things were OK later that day. Very thoughtful. The gentleman that works the parking garage gate was especially nice and had great recommendations for local spots. The location is close to freeways if you are traveling around. "
Aimee 3-night trip
Posted 6 days ago
Courtyard by Marriott Waterbury Downtown

Explore a world of travel with Expedia

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.