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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 380 Vacation Homes in Middletown with updated reviews, rates, and availability.

Waterfront House with picture-perfect views from all 3 levels.
Interior

Waterfront House with picture-perfect views from all 3 levels.

9.8 out of 10, Exceptional, (81)
"We had an amazing weekend celebrating my husbands birthday. The house was perfect. The view was priceless. The beach was amazing. It was the first time we were able to travel with our dog, and he had the best time at the beach. We will be returning for another vacation for sure. "
Waterfront House with picture-perfect views from all 3 levels.
Stylish & Luxurious 3 BDR Home with Play Station
Fridge, microwave, oven, stovetop

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station
Large Charming Historic House close to Beaches
Fridge, microwave, oven, dishwasher

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (23)
"This was the BEST decision for our family. The house was very cozy, old charm feel with some modern updates. The downstairs bathroom had a Spa vibe. We loved the 6 bedrooms & spacious kitchen & dining room. Loved how close it was to food & entertainment. The walk to the beach was only 10 minutes & very safe. We are use to blinds and/or shades, so just having light curtains for the windows was"
Large Charming Historic House close to Beaches
Cozy Westbrook Vacation Rental - Walk to Beach!
Aerial view

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (13)
"Perfect off season weekend for us with easy access to walks on the beach and lots of relaxing!"
Cozy Westbrook Vacation Rental - Walk to Beach!
New Madison beach house - Ocean front- Great views- booking Summer 2025
Exterior

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (56)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025
Lakefront Getaway w Hot Tub, Game Room & Views - Pet-Friendly
Outdoor spa tub

Lakefront Getaway w Hot Tub, Game Room & Views - Pet-Friendly

10.0 out of 10, Exceptional, (1)
"Beautiful view from the upstairs window. I enjoyed the pellet stove on the cold days."
The price is AED 680
AED 1,314 total
includes taxes & fees
21 Apr - 22 Apr
Lakefront Getaway w Hot Tub, Game Room & Views - Pet-Friendly
Waterfront Beach House
Terrace/patio

Waterfront Beach House

9.6 out of 10, Exceptional, (42)
"The property is nicely located on the water and convenient to many attractions. "
Waterfront Beach House
Luxe Lake House in Connecticut
Fridge, microwave, oven, stovetop

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"The house easily accommodated my friends and family for a weekend of relaxation. The place is very spacious with all modern amenities. We especially loved waking up to the gorgeous view of the lake in the back. The views were breathtaking. Would definitely consider going back. "
The price is AED 1,458
AED 3,542 total
includes taxes & fees
6 Apr - 7 Apr
Luxe Lake House in Connecticut
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun loungers, beach towels

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (88)
"Tuvimos un finde increíble en la casa, súper cómoda y bonita "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort
Fridge, microwave, oven, stovetop

Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

10.0 out of 10, Exceptional, (55)
"Lovely, spacious and clean. We spent our Christmas holiday together with our family and the house was spacious and spotless. We had 5 adults with 2 small children in house. We hosted Christmas dinner for us and local family. Great space. Would love to rent in summer months to utilize outdoor space"
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (15)
"This is such a great property, I spent a whole month with three separate stays adjacent due to travel planning and the host was wonderful. The house is really beautiful and in a great neighborhood and it’s very comfortable and super clean. This will be a regular for me in the Hartford area. I’m looking forward to seeing what the beautiful landscaping is like in the spring and summer too."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Waterfront Lakehouse in Clinton, CT with Hot Tub!
Outdoor spa tub

Waterfront Lakehouse in Clinton, CT with Hot Tub!

7.0 out of 10, Good, (2)
"My family and I absolutely loved our stay at this home! It was the perfect retreat for us, and we thoroughly enjoyed the hot tub and the breathtaking sunset views, especially while cooking in the beautifully designed kitchen. The kitchen was fully equipped, making it easy to prepare an amazing family dinner. The town of Clinton was absolutely charming, with the friendliest people, and we fell in love with Hammonasset Beach—it’s a must-visit! We’ll definitely be returning in the summer. The...
Waterfront Lakehouse in Clinton, CT with Hot Tub!
Grammy's Lake House w/ Private Waterfront Access
Interior

Grammy's Lake House w/ Private Waterfront Access

9.6 out of 10, Exceptional, (11)
"The home was beautiful. Some of the furniture was old and it shouldn’t be sat on plenty of room for family plenty of games to play beautiful electricfireplace,beautiful view! The beds were uncomfortable and a few things needed to be updated."
Grammy's Lake House w/ Private Waterfront Access
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Beach nearby, sun loungers, beach towels

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Outdoor pool

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (7)
"It was a great house to host our family for Thanksgiving dinner! "
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (19)
"Very nice clean house. Felt like coming home after work"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (2)
"Same day check in info, not provided the day before like most hosts "
The price is AED 823
AED 2,252 total
includes taxes & fees
9 Apr - 10 Apr
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
WeHa Oak Haven
Private kitchen

WeHa Oak Haven

10.0 out of 10, Exceptional, (4)
"I had a great stay in West Hartford with my 17 year old daughter. The property is conveniently located in West Hartford and also a quick drive to the University of Hartford, which we visit for an Art School event. The host is fantastic, provides great communication and simple check-in/ check-out process. The parking spot is ample and the home was comfortable and just as described. We will book this place again and highly recommend! "
WeHa Oak Haven
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (4)
"We came to the area for a long weekend event at Wesleyan University. I had never booked through VRBO and was not familiar with the process. From my first communication with Gilbert I felt like I was going to visit family. He was amazing to communicate with provided information about the area and the process and was super accommodating when he learned our flight was arriving early. From the moment we stepped through the door we knew our stay would be special. The home is beautiful, beds...
The price is AED 514
AED 891 total
includes taxes & fees
28 Apr - 29 Apr
Family Stays: Middletown, CT
Beautiful 4BR Beach House with Private Beach Access.
Beach nearby, beach towels

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.
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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Other property types in Middletown

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a GREAT time here!! Just beautiful scenery all around. The cabin was well equipped with everything we needed essentially. I was quite impressed with how comfortable we actually were. There was a temporary power outage but it didn’t last long and management not only delivered more wood to us but also gave it to us for free as we wanted to spend our time outdoors during the outage. Im super happy to have had this experience and would absolutely be doing it again!! Thank you Postcard...
The price is AED 496
AED 570 total
includes taxes & fees
29 Apr - 30 Apr
Postcard Cabins Machimoodus
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun loungers, beach towels

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (88)
"Tuvimos un finde increíble en la casa, súper cómoda y bonita "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Cozy Westbrook Vacation Rental - Walk to Beach!
Aerial view

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (13)
"Perfect off season weekend for us with easy access to walks on the beach and lots of relaxing!"
Cozy Westbrook Vacation Rental - Walk to Beach!
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.