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Middletown Vacation Rentals

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Vacation Rentals in Middletown

#24 *Serenity* A Lakefront Cottage Retreat

9.8 out of 10, Exceptional, (18)
"Quiet and peaceful cottage. Clean and well equipped with everything we needed. Great location to sight see and visit local attractions. Loved sitting relaxing by the lake."
The price is CA $194
CA $446 total
includes taxes & fees
Aug 6 - Aug 7
#24 *Serenity* A Lakefront Cottage Retreat

Postcard Cabins Machimoodus

2.0 star property
9.4 out of 10, Exceptional, (45)
"Great stay"
The price is CA $192
CA $276 total
includes taxes & fees
Aug 6 - Aug 7
Postcard Cabins Machimoodus

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (39)
"My wife and I loved our weekend stay at this cabin!"
The price is CA $465
CA $860 total
includes taxes & fees
Sep 2 - Sep 3
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Shoreline Oasis

8.8 out of 10, Excellent, (5)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is CA $247
CA $362 total
includes taxes & fees
Sep 4 - Sep 5
Shoreline Oasis

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (28)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is CA $185
CA $357 total
includes taxes & fees
Sep 2 - Sep 3
1-bedroom cottage with Grove Beach 🏖️ access.

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.

Charming Westbrook Cottage, Steps to Private Beach

9.8 out of 10, Exceptional, (6)
"Had a great stay!"
Charming Westbrook Cottage, Steps to Private Beach

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

2.0 star property
9.0 out of 10, Wonderful, (8)
"Beautiful location, very comfortable for our small family."
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Owner didn’t respond to messages and there was issues with the virtual key QR code However after check in everything was wonderful and I had no issues "
The price is CA $159
CA $234 total
includes taxes & fees
Aug 10 - Aug 11
Cozy apartment in charming Hartford with AC, WiFi

DIRECT WATERFRONT PRIVATE BEACH

9.4 out of 10, Exceptional, (23)
"This rental was perfect. Super clean and comfy with the most amazing views. Loved that it’s right on the water with a private beach. We will definitely book this property again."
DIRECT WATERFRONT PRIVATE BEACH

Exclusive Midweek Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (65)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Midweek Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

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

Waterfront Estate Home - Beach and Shared Pool - East

9.8 out of 10, Exceptional, (43)
"Perfect home for a big family gathering!"
Waterfront Estate Home - Beach and Shared Pool - East

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (35)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Beachside Branford- walk to Beach, Grill

9.8 out of 10, Exceptional, (6)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (16)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is CA $744
CA $1,218 total
includes taxes & fees
Aug 18 - Aug 19
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

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

10.0 out of 10, Exceptional, (64)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.4 out of 10, Exceptional, (8)
"I was a little worried to be right in downtown with just me and my daughter. But this location was very safe and cute shopping area around the apartment. "
The price is CA $150
CA $224 total
includes taxes & fees
Aug 10 - Aug 11
Totally Private Cozy studio in awesome Hartford with WiFi, AC
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

Frequently asked questions

Are there vacation rentals in Middletown?

Yes, you can find vacation rentals in Middletown close to Kidcity Children's Museum, or you can choose a more remote option if you want a relaxing stay. Middletown is known for its entertainment choices and festivals. Make sure you have time to check out the basketball games and university setting during your trip.

What are some of the best vacation rentals that Middletown has to offer?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This vacation home rental outside of Middletown is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a hot tub.

How many vacation rentals are there in Middletown?

With 12 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Family-friendly attractions include Kidcity Children's Museum and Van Vleck Observatory, whereas Wadsworth Falls State Park and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and General Mansfield House.

What’s a vacation rental in Middletown like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Middletown. Vacation rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.