A forested landscape with a winding dirt road and power lines.

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Check availability on Middletown Romantic Hotels

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

Our top choices for Middletown romantic hotels

A lakeside setting with a row of colorful kayaks and a sailboat docked.

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
10.0 out of 10, Exceptional, (156 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
The price is AED 753
AED 1,418 total
includes taxes & fees
26 Jul - 27 Jul
Go Jump in the Lake!
Terrace/patio

Peek-A-Boo View, Amston Lake

Peek-A-Boo View, Amston Lake
Lebanon
9.8 out of 10, Exceptional, (51 reviews)
"Everything was perfect! "
United States
Melissa R.
The price is AED 753
AED 1,425 total
includes taxes & fees
27 Jul - 28 Jul
Peek-A-Boo View, Amston Lake
Terrace/patio

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Clinton
10.0 out of 10, Exceptional, (30 reviews)
"It was a very clean well kept property. The accommodation was very comfortable. We all truly enjoyed the house and location. "
United States
claire
The price is AED 4,771
AED 7,551 total
includes taxes & fees
31 Jul - 1 Aug
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
TV

All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
The price is AED 433
AED 1,071 total
includes taxes & fees
10 Jul - 11 Jul
All New Private and Cozy in great location
Outdoor dining

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (67 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,146
AED 1,931 total
includes taxes & fees
7 Jul - 8 Jul
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"I stayed at the Omni for my 50th reunion at Yale. Its location on the green is perfect, convenient to Yale and New Haven landmarks. It is a bit pricey, but worth the cost."
Jean 2-night trip
Posted 3 hours ago
Omni New Haven Hotel at Yale

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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 General Mansfield House, Van Vleck Observatory, or Wadsworth Mansion. 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 General Mansfield House, Van Vleck Observatory, or Wadsworth Mansion.
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.