Photo by Simmie Reagor
Search Vacation Homes in Middletown
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 392 Vacation Homes in Middletown with updated reviews, rates, and availability.

Waterfront House with picture-perfect views from all 3 levels.
Waterfront House with picture-perfect views from all 3 levels.
9.8 out of 10, Exceptional, (82)

Stylish & Luxurious 3 BDR Home with Play Station
Stylish & Luxurious 3 BDR Home with Play Station
9.4 out of 10, Exceptional, (9)

Large Charming Historic House close to Beaches
Large Charming Historic House close to Beaches
9.6 out of 10, Exceptional, (23)

Cozy Westbrook Vacation Rental - Walk to Beach!
Cozy Westbrook Vacation Rental - Walk to Beach!
10.0 out of 10, Exceptional, (14)

New Madison beach house - Ocean front- Great views- booking Summer 2025
New Madison beach house - Ocean front- Great views- booking Summer 2025
10.0 out of 10, Exceptional, (57)

Lakefront Cottage - Hot Tub, Game Room & Scenic Views
Lakefront Cottage - Hot Tub, Game Room & Scenic Views
10.0 out of 10, Exceptional, (3)

Waterfront Beach House
Waterfront Beach House
9.6 out of 10, Exceptional, (42)

Luxe Lake House in Connecticut
Luxe Lake House in Connecticut
10.0 out of 10, Exceptional, (2)
The price is SAR 1,375
SAR 3,473 total
includes taxes & fees
21 Apr - 22 Apr
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Middletown

Postcard Cabins Machimoodus
Postcard Cabins Machimoodus
10.0 out of 10, Exceptional, (7)
The price is SAR 388
SAR 598 total
includes taxes & fees
30 Apr - 1 May

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (128)

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕
9.8 out of 10, Exceptional, (128)
The price is SAR 1,355
SAR 2,602 total
includes taxes & fees
6 May - 7 May
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.
Recent reviews of Middletown hotels
Recent reviews of Middletown hotels

New Haven Hotel
5/5 Excellent
"Easy checkin and parking. "
A verified traveler stayed at New Haven Hotel
Posted 1 day ago