Middletown Holiday Rentals: Short-Term Accommodations for Rent

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Holiday Rentals in Middletown

"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."

HK$2,746 total

includes taxes & fees

3 Sept - 4 Sept

"Great stay"

HK$1,656 total

includes taxes & fees

18 Aug - 19 Aug

"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!"

HK$2,015 total

includes taxes & fees

26 Aug - 27 Aug

"Loved the overall stay and experience. The private beach access is a bonus"

HK$1,972 total

includes taxes & fees

18 Aug - 19 Aug

"My wife and I loved our weekend stay at this cabin!"

HK$5,235 total

includes taxes & fees

26 Aug - 27 Aug

"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! "

"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. "

HK$1,272 total

includes taxes & fees

31 Aug - 1 Sept

"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. "

"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 "

HK$1,326 total

includes taxes & fees

24 Aug - 25 Aug

"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. "

HK$2,362 total

includes taxes & fees

22 Aug - 23 Aug

"Perfect home for a big family gathering!"

"Beautiful location, very comfortable for our small family."

"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. "

"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."

"Great location "

4 bedrooms, iron/ironing board, free WiFi, bed sheets

"Stunning cottage! Great location. Well-equipped kitchen! Comfy beds. Loved the views! Truly a special place!"

"This home is absolutely beautiful and well-equipped. It was perfect for my quick weekend getaway. The location is fantastic. Robin made sure we had what we needed. Highly recommend. "

"Loved the feeling of being in a family cottage near the beautiful water and pretty old homes "

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Top Middletown Hotel Reviews

The Capitol Hotel

10/10 Excellent

"The rooms were great, and the staff was helpful. The underground garage is VERY difficult to get out of. I had to do a 7-point turn, then found I was aimed the wrong way and did another difficult 7-point turn to get turned around before leaving."

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

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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.

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Middletown Holiday Rentals

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Holiday Rentals in Middletown

#24 Serenity A Lakefront Cottage Retreat

Postcard Cabins Machimoodus

Shoreline Oasis

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

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The Beach Nest-Lux Cottage Steps to the Beach

DIRECT WATERFRONT PRIVATE BEACH

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

Waterfront Cottage in Branford

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

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