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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Our top choices for Middletown vacation rentals

#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 $217
CA $477 total
includes taxes & fees
Sep 3 - Sep 4
#24 *Serenity* A Lakefront Cottage Retreat

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (50)
"Great stay"
The price is CA $207
CA $293 total
includes taxes & fees
Aug 21 - Aug 22
Postcard Cabins Machimoodus

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"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 $364 total
includes taxes & fees
Sep 1 - Sep 2
Shoreline Oasis

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (29)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is CA $160
CA $326 total
includes taxes & fees
Sep 1 - Sep 2
1-bedroom cottage with Grove Beach 🏖️ access.

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

10.0 out of 10, Exceptional, (40)
"My wife and I loved our weekend stay at this cabin!"
The price is CA $468
CA $918 total
includes taxes & fees
Aug 26 - Aug 27
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

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

10.0 out of 10, Exceptional, (139)
"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

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 $151
CA $225 total
includes taxes & fees
Aug 31 - Sep 1
Totally Private Cozy studio in awesome Hartford with WiFi, AC

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

9.8 out of 10, Exceptional, (66)
"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 Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (3)
"All was as advertised. The Xfinity INDOOR theatre us across the the street. Xfinity OUTDOOR theatre/ arena is only about a .8 mile walk away. We took an UBER there and walked back after our concert"
The price is CA $159
CA $235 total
includes taxes & fees
Aug 24 - Aug 25
Cozy apartment in charming Hartford with AC, WiFi

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

9.6 out of 10, Exceptional, (93)
"Our family had a fabulous week at the beach celebrating my 70th birthday. Lots of fun, food and laughter with the ocean as our background. This beach house had everything we needed as was as comfortable as our own home. "
Waterfront House with picture-perfect views from all 3 levels.

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

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

2.0 star property
9.4 out of 10, Exceptional, (11)
"Beautiful location, very comfortable for our small family."
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

Relaxing summer rental, walking distance to the beach, short ride to the outlets

9.8 out of 10, Exceptional, (48)
"Very pleased with this stay. Perfect for us and the kids. Super cute beach home."
Relaxing summer rental, walking distance to the beach, short ride to the outlets

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)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
The Beach Nest-Lux Cottage Steps to the Beach

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had a great stay at the beach house! Luanne was a super-responsive host and communication with her throughout the stay through the app was a breeze. "
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.6 out of 10, Exceptional, (10)
"Beautiful area, close to the beach, with a wonderfully kept house."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

10.0 out of 10, Exceptional, (3)
"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."
The price is CA $186
CA $330 total
includes taxes & fees
Aug 21 - Aug 22
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (28)
"Had a wonderful stay. The house was large enough to allow us all to have our own rooms. Location was perfect and within walking distance of everything. "
Large Charming Historic House close to Beaches

Conference Room Rental no sleeping arrangements

The price is CA $994
CA $1,285 total
includes taxes & fees
Aug 21 - Aug 22
Conference Room Rental no sleeping arrangements
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?

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi: This vacation home rental outside of Middletown is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.