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Middletown Holiday Rentals

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Holiday 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 NZ$595
includes taxes & fees
3 Sept - 4 Sept
#24 *Serenity* A Lakefront Cottage Retreat

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (47)
"Great stay"
The price is NZ$355
includes taxes & fees
14 Aug - 15 Aug
Postcard Cabins Machimoodus

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 NZ$1,123
includes taxes & fees
26 Aug - 27 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Shoreline Oasis

9.0 out of 10, Wonderful, (6)
"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 NZ$433
includes taxes & fees
26 Aug - 27 Aug
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 NZ$451
includes taxes & fees
27 Aug - 28 Aug
1-bedroom cottage with Grove Beach 🏖️ access.

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

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

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

10.0 out of 10, Exceptional, (137)
"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.

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 NZ$274
includes taxes & fees
31 Aug - 1 Sept
Totally Private Cozy studio in awesome Hartford with WiFi, AC

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

The price is NZ$507
includes taxes & fees
23 Aug - 24 Aug
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

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 NZ$285
includes taxes & fees
17 Aug - 18 Aug
Cozy apartment in charming Hartford with AC, WiFi

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

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, (18)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is NZ$1,375
includes taxes & fees
18 Aug - 19 Aug
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, (65)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Go Jump in the Lake!

10.0 out of 10, Exceptional, (143)
"Perfect for our family. Close to the lake and beaches. We enjoyed our stay."
Go Jump in the Lake!
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 holiday rentals in Middletown?

Yes, there are holiday rentals in Middletown close to Kidcity Children's Museum, or you can select a more secluded option if you're looking for 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 holiday rentals that Middletown has to offer?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This holiday home rental outside Middletown is located on the beach, and has an outdoor pool, a balcony and a BBQ 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 1 hot tub.

How many holiday rentals are there in Middletown?

With 13 Expedia holiday rentals, you're guaranteed 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 holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.