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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Our top choices for Middletown vacation rentals

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (63)
"Great place "
$136 nightly
The price is $157
Sep 15 - Sep 16
Total with taxes and fees
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!"
$230 nightly
The price is $261
Sep 11 - Sep 12
Total with taxes and fees
Shoreline Oasis

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

10.0 out of 10, Exceptional, (44)
"Amazing property, we loved everything about it, highly recommended, will stay again "
$617 nightly
The price is $698
Sep 14 - Sep 15
Total with taxes and fees
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

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

9.4 out of 10, Exceptional, (13)
"Beautiful area, close to the beach, with a wonderfully kept house."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

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

10.0 out of 10, Exceptional, (144)
"Had a great time - perfect stay for a weekend getaway! The well appointed studio has everything you need and very convenient to restaurants & shopping in town. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.2 out of 10, Wonderful, (10)
"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. "
$150 nightly
The price is $170
Sep 11 - Sep 12
Total with taxes and fees
Totally Private Cozy studio in awesome Hartford with WiFi, AC

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (29)
"Always a pleasure staying here!"
$192 nightly
The price is $217
Sep 30 - Oct 1
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

Charming Studio| Near Yale| Downtown New Haven

10.0 out of 10, Exceptional, (3)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
$215 nightly
The price is $215
Sep 24 - Sep 25
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven

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

9.8 out of 10, Exceptional, (66)
"This home was perfect for a quiet stay on the Connecticut coast. Every couple had their own bed and bath. Beautiful view. Very clean. Open floor plan. Lovely area to walk or jog. If we return to this area, this is where we will stay! "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

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

9.8 out of 10, Exceptional, (48)
"great friendly neighborhood , great beach , nice and clean, comfy beds had a great time"
Relaxing summer rental, walking distance to the beach, short ride to the outlets

New Furnished Apt in West Hartford w/ Parking and Central AC

9.0 out of 10, Wonderful, (2)
"Good communication with the manager, quiet place and extremely clean. I enjoyed it"
$204 nightly
The price is $231
Sep 15 - Sep 16
Total with taxes and fees
New Furnished Apt in West Hartford w/ Parking and Central AC

Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

2.0 out of 10, (1)
"Host never emailed info. After numerous attempts to contact them, we gave up and stayed in a hotel. VRBO gave full refund. I don’t recommend this host, but VRBO was great!"
$267 nightly
The price is $302
Sep 11 - Sep 12
Total with taxes and fees
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

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

10.0 out of 10, Exceptional, (66)
"Delightful to be on the water, spacious house for a family, responsive owner, a worthwhile trip! "
New Madison beach house - Ocean front- Great views- booking Summer 2025

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

9.6 out of 10, Exceptional, (93)
"We were attending a family wedding at Waters Edge so the location to facility was perfect. Also very convenient to Town of Westbrook"
Waterfront House with picture-perfect views from all 3 levels.

Conference Room Rental no sleeping arrangements

$823 nightly
The price is $931
Sep 11 - Sep 12
Total with taxes and fees
Conference Room Rental no sleeping arrangements

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

10.0 out of 10, Exceptional, (68)
"The home worked out well. It was nicely decorated and the kitchen/family room was perfect for us."
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

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

2.0 star property
10.0 out of 10, Exceptional, (5)
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

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 14 - Sep 15
Total with taxes and fees
Cozy apartment in charming Hartford with AC, WiFi

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

10.0 out of 10, Exceptional, (2)
" Heck-on was smooth and the kitchen and facilities were great. "
$258 nightly
The price is $293
Sep 22 - Sep 23
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

Family Gem on Dyer Street

$776 nightly
The price is $879
Sep 23 - Sep 24
Total with taxes and fees
Family Gem on Dyer Street
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 $157 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?

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.