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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (54)
"Great stay"
$154 nightly
The price is $177
Aug 28 - Aug 29
Total with taxes and fees
Postcard Cabins Machimoodus

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

10.0 out of 10, Exceptional, (140)
"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

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!"
$230 nightly
The price is $261
Aug 31 - Sep 1
Total with taxes and fees
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"
$206 nightly
The price is $234
Sep 1 - Sep 2
Total with taxes and fees
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, (43)
"Amazing property, we loved everything about it, highly recommended, will stay again "
$617 nightly
The price is $698
Sep 1 - Sep 2
Total with taxes and fees
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.2 out of 10, Wonderful, (9)
"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. "
$144 nightly
The price is $163
Aug 31 - Sep 1
Total with taxes and fees
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

Seven Sleeps + Patio retreat/lake + Two-in-one game table/PS5

10.0 out of 10, Exceptional, (1)
"This place was very clean and Michael was great, answering all my questions quickly. check in was simple just a code to get in it was very updated and the beds were very comfortable. It was close to Yale and to some great pizza places"
Seven Sleeps + Patio retreat/lake + Two-in-one game table/PS5

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.

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"
$150 nightly
The price is $170
Sep 7 - Sep 8
Total with taxes and fees
Cozy apartment in charming Hartford with AC, WiFi

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

10.0 out of 10, Exceptional, (59)
"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. "
$401 nightly
The price is $454
Aug 28 - Aug 29
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Family Gem on Dyer Street

$823 nightly
The price is $931
Sep 3 - Sep 4
Total with taxes and fees
Family Gem on Dyer Street

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

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (80)
"This was a great property and close to many things to see and visit. The welcome note and goodies were much appreciated. Great communication from the host!!!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

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

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

10.0 out of 10, Exceptional, (32)
"Very much enjoyed our stay!"
$278 nightly
The price is $314
Aug 28 - Aug 29
Total with taxes and fees
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

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

UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

10.0 out of 10, Exceptional, (65)
"We really enjoyed our stay at the property. The home was very clean, the beds were comfortable, and the location was convenient for all of our weekend activities."
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

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

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

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

2.0 star property
10.0 out of 10, Exceptional, (4)
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
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

Find out more about Middletown

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.