Photo by Simmie Reagor

Find Romantic Hotels in Middletown, CT from $77

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

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Middletown Romantic Hotels

This weekend
Next weekend

Top Middletown Romantic Hotels

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
$161 nightly
The price is $182
Dec 3 - Dec 4
Total with taxes and fees
Inn at Middletown

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
$80 nightly
The price is $92
Dec 25 - Dec 26
Total with taxes and fees
New Haven Hotel

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
$67 nightly
The price is $77
Dec 20 - Dec 21
Total with taxes and fees
Courtyard by Marriott Waterbury Downtown

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
$138 nightly
The price is $159
Dec 3 - Dec 4
Total with taxes and fees
Avon Old Farms Hotel

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
$166 nightly
The price is $191
Dec 9 - Dec 10
Total with taxes and fees
Water's Edge Resort & Spa

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
$146 nightly
The price is $162
Dec 9 - Dec 10
Total with taxes and fees
Westbrook Inn B&B

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
$151 nightly
The price is $174
Dec 3 - Dec 4
Total with taxes and fees
Omni New Haven Hotel at Yale

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
$111 nightly
The price is $128
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Cheshire - Southington by IHG

HYATT house Hartford North/Windsor

3.0 star property
Windsor
9.0 out of 10, Wonderful, (1012)
"Amazing stay "
United States
Amber
$120 nightly
The price is $138
Jan 2 - Jan 3, 2026
Total with taxes and fees
HYATT house Hartford North/Windsor

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (338)
"Staff and hotel are lovely "
United States
Steven
$245 nightly
The price is $282
Dec 9 - Dec 10
Total with taxes and fees
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.

Black Friday Sale

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

Find out more about Middletown

Middletown attractions for couples

Middletown, Connecticut, offers a delightful blend of culture, adventure, and relaxation for travelers seeking quality experiences. Start your journey at the stunning Wadsworth Falls State Park, where you can hike scenic trails and enjoy the breathtaking views of the cascading waterfalls. Families will appreciate the hands-on exhibits at the Kidcity Children's Museum, a vibrant space designed to spark creativity and imagination in young minds. For a taste of local history, visit the Connecticut River Museum, where you can explore interactive displays that tell the story of the river's significance to the region. Food enthusiasts will love the culinary delights at the local farmers market, featuring fresh produce and artisanal goods that showcase the flavors of Connecticut. After a day of exploration, unwind in the charming downtown area, filled with boutique shops and inviting eateries. Consider staying at one of the well-reviewed hotels along Main Street, where you can enjoy the convenience of being close to attractions, along with attentive service and comfortable accommodations that cater to your family's needs. Each stay promises an enjoyable experience, allowing you to recharge for another day of adventure in this vibrant city.

Top Middletown Hotel Reviews

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.

Explore a world of travel with Expedia