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Middletown Holiday Rentals

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Check prices for these dates

Tonight
18 Jul - 19 Jul
Tomorrow
19 Jul - 20 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Middletown

Postcard Cabins Machimoodus
Escape to a serene forest retreat with a cozy fire pit and comfortable Adirondack chairs.

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (37)
"Great stay"
Postcard Cabins Machimoodus
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

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

10.0 out of 10, Exceptional, (133)
"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
Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

Shoreline Oasis

8.0 out of 10, Very good, (2)
"The house and town were adorable. The space was the second floor. It was clean and and comfortable. "
Shoreline Oasis
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Surrounded by lush greenery, this cabin features a cozy porch with seating and a stone pathway leading to the entrance.

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

10.0 out of 10, Exceptional, (36)
"My wife and I loved our weekend stay at this cabin!"
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Walk To Goodspeed Opera House!
Welcome to Goodspeed Opera House, featuring a grand double door entrance with symmetrical design and large windows.

Walk To Goodspeed Opera House!

9.6 out of 10, Exceptional, (25)
"This property was in a great location for going to the Goodspeed opera house. "
Walk To Goodspeed Opera House!
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi
Enjoy serene lakeside views from the wooden pier, surrounded by rolling hills and a natural stone wall.

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

2.0 star property
8.4 out of 10, Very good, (5)
"Beautiful location, very comfortable for our small family."
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Relax on the covered porch with a view of the sea, featuring a comfortable seating area with two chairs.

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

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Charming Westbrook Cottage, Steps to Private Beach
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and refrigerator.

Charming Westbrook Cottage, Steps to Private Beach

9.8 out of 10, Exceptional, (6)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
Cozy apartment in charming Hartford with AC, WiFi
Cozy apartment with a kitchenette, featuring a stove, sink, and cabinets. The room includes a bed with a wooden frame, two windows, and a small table with a chair.

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (1)
Cozy apartment in charming Hartford with AC, WiFi
1-bedroom cottage with Grove Beach 🏖️ access.
Relax in comfort with a sofa, throw blanket, and natural light pouring in through the large window.

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (26)
"Loved the overall stay and experience. The private beach access is a bonus"
1-bedroom cottage with Grove Beach 🏖️ access.
Lux Boutique Large Private LOFT Pratt St Hartford
Enjoy a compact yet functional space with a kitchenette, dining area, and cozy living space featuring a sofa and flat-screen TV.

Lux Boutique Large Private LOFT Pratt St Hartford

9.0 out of 10, Wonderful, (17)
"I am impressed with the Lux Private Loft. Absolutely Gorgeous!!. I hope to return. The kitchen area, enormous shower, large screen t.v. I will book again as soon as possible."
Lux Boutique Large Private LOFT Pratt St Hartford
Waterfront House with picture-perfect views from all 3 levels.
Enjoy a serene sea view from the large window, accompanied by comfortable seating and a small table.

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

9.6 out of 10, Exceptional, (90)
"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.
The Beach Nest-Lux Cottage Steps to the Beach
Stunning living area with a spiral staircase, dining table, and modern kitchen.

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
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Relax on the deck with a scenic view of the water and shoreline.

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (45)
"Home was very comfortable and a great location. The views were spectacular. Owner gave us great recommendations for restaurants and nearby attractions. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort
Pathway leads to serene views of the surrounding landscape.

Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

10.0 out of 10, Exceptional, (61)
"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 kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort
New Madison beach house - Ocean front- Great views- booking Summer 2025
Enjoy waterfront views and beach access from this coastal property.

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

10.0 out of 10, Exceptional, (62)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa
Enjoy meals in this kitchen with a microwave, stainless steel range hood, and dining area with a table and chairs.

Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

2.0 star property
6.6 out of 10, (4)
"Communication with the host was excellent. His place was clean, bright, and very well equipped! The location makes it easy to get around the greater Hartford area. Our stay was very good!"
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa
Modern Condo|DWNTN Hartord| XL Center| GYM
Enjoy cooking in this well-equipped kitchen with a microwave, coffee maker, and coffee machine.

Modern Condo|DWNTN Hartord| XL Center| GYM

4.0 out of 10, (1)
"The location was fantastic.Check-In, Parking and Check-Out easy.The images of the condo were misleading.- cockroaches were present- Floors were not swept- sofa bed sheets were still on bed and unwashed- makeup on the pillow cases from the pullout couch and the hair dryer bag- bedside furniture had broken drawers- one kitchen chair was extremely wobbly- kitchen table light did not workWe will not staying here again."
Modern Condo|DWNTN Hartord| XL Center| GYM
Heavenly Home in New Haven /5 mins drive from Yale
Fridge, microwave, oven, stovetop

Heavenly Home in New Haven /5 mins drive from Yale

9.0 out of 10, Wonderful, (19)
"Place was so cute and spacious. Owner was awesome too! Definitely recommend."
Heavenly Home in New Haven /5 mins drive from Yale
Go Jump in the Lake!
Explore serene lakeside tranquility with a variety of canoes available for use.

Go Jump in the Lake!

10.0 out of 10, Exceptional, (141)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"I love! Everything so good and the breakfast is yummy!! My family love the hotel ❣️"
Coralisse 1-night trip
Posted 2 days ago
Hampton Inn & Suites Hartford/East Hartford

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 of 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 11 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 Connecticut Valley Railroad State Park Trail.

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.