Photo by Simmie Reagor

Search Vacation Homes in Middletown

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Middletown

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Very comfortable rockers and Adirondack chairs make it easy to relax and enjoy the lake view. Our bed was comfortable, and Nile supplied all we needed with linens and soaps. We appreciated all the space and large dining table. Lake is beautiful. Very enjoyable stay. Exceptional communication with our host. "
Grammy's Lake House w/ Private Waterfront Access

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

10.0 out of 10, Exceptional, (58)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is AED 955
AED 1,669 total
includes taxes & fees
10 Aug - 11 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan

2.0 star property
10.0 out of 10, Exceptional, (6)
"Everything about our stay at this property was great. Communication, check-in, cleanliness, etc. The location is directly across the street from Wesleyan University which made my son's visit all the better. I will definately stay here again."
New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

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

9.6 out of 10, Exceptional, (92)
"It was a very nice stay. Sound of the ocean was calming. We would go back. "
Waterfront House with picture-perfect views from all 3 levels.

The Beach Nest-Lux Cottage Steps to the Beach

9.8 out of 10, Exceptional, (6)
"Quick weekend stay as we needed to be in the area for a soccer tournament. The house was super clean and had everything we needed. Would definitely stay again. "
The Beach Nest-Lux Cottage Steps to the Beach

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (31)
"This a the most unique place! A very clean and comfortable apartment above a barn with beautiful horses and more. Wonderful hosts too. We hope to be back! "
Mountaintop Horse Farm with Heated Pool

Gorgeous 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (74)
"We loved our stay at this beautiful cottage. The entire experience was very smooth, from pre-check in to getting there and even offers to help with anything we needed in our stayThe cottage is very cozy and well-cared for. The rooms are comfortable and the Internet fast. There is a lot to do in the area, with New Haven nearby and many good restaurants."
Gorgeous 4BR Beach House with Private Beach Access.

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

9.8 out of 10, Exceptional, (47)
"Clean cottage, more spacious than it looks. Perfect fenced back yard for family pets. Quiet neighborhood and easy walk to beach. Stayed at this cottage for a month as our home needed some repairs. Extremely comfortable for my husband, miniature poodle and I. Hosts were very gracious and accommodating!! Would have stayed longer if available. "
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

Modern Luxury, The Perfect Getaway Awaits

10.0 out of 10, Exceptional, (2)
"Super clear, spacious, house looks just like the photos. Very easy communication with the host. Thank you!"
The price is AED 1,080
AED 1,958 total
includes taxes & fees
11 Aug - 12 Aug
Modern Luxury, The Perfect Getaway Awaits

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks

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

9.4 out of 10, Exceptional, (23)
"Right off the highway, very clean and kitchen was very well equipped. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Beach community with private beaches

10.0 out of 10, Exceptional, (11)
"We had a wonderful week staying here with my family. It was family friendly, clear, had everything we needed and was a 10 min walk from beach!"
Beach community with private beaches

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (27)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade

Private Apartment in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
The price is AED 498
AED 1,532 total
includes taxes & fees
14 Aug - 15 Aug
Private Apartment in Berlin

Family Gem on Dyer Street

The price is AED 1,504
AED 3,339 total
includes taxes & fees
11 Aug - 12 Aug
Family Gem on Dyer Street

Modern & Cozy Cape | 4 Bedroom House | Central Location

10.0 out of 10, Exceptional, (5)
"We had a great stay in this house. It provided everything we needed for a comfortable and enjoyable visit. All the rooms were clean, tidy, and well-maintained, creating a welcoming environment. The host was exceptionally helpful and quick to respond to any questions or needs we had, which made our experience even better. We highly recommend this house for anyone looking for a hassle-free and pleasant stay."
The price is AED 514
AED 1,135 total
includes taxes & fees
12 Aug - 13 Aug
Modern & Cozy Cape | 4 Bedroom House | Central Location

Prime West Hartford Center: Timeless Charm

10.0 out of 10, Exceptional, (17)
"Very comfortable and clean accommodations in walking distance to stores and many restaurant options. Highly recommend for anyone needing lodging in West Hartford. "
Prime West Hartford Center: Timeless Charm

Spacious 4-bedroom house with AC, WiFi in welcoming Guilford

10.0 out of 10, Exceptional, (2)
" The house was awesome, had an very good layout, great yard, nice deck and it was the perfect place for our group! Great communication with the owner!"
Spacious 4-bedroom house with AC, WiFi in welcoming Guilford

Private Yard & Covered Deck: Vintage Windsor Home

9.0 out of 10, Wonderful, (8)
"Great rentsl. The location was convenient to the airport. The house was clean and well kept. "
Private Yard & Covered Deck: Vintage Windsor Home
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

Top Middletown Hotel Reviews