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Middletown Holiday Rentals

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Check prices for these dates

Tonight
30 Jun - 1 Jul
Tomorrow
1 Jul - 2 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Holiday Rentals in Middletown

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
9.8 out of 10, Exceptional, (31)
"Great stay"
The price is HK$1,170
HK$1,661 total
includes taxes & fees
7 Jul - 8 Jul
Postcard Cabins Machimoodus
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (131)
"My husband and I had a wonderful time at this idyllic cottage on the water in Branford. Great location and hosts. Beautiful community for long walks, restaurants nearby. Highly recommend! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Shoreline Oasis
Exterior

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is HK$1,405
HK$2,069 total
includes taxes & fees
6 Jul - 7 Jul
Shoreline Oasis
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Exterior

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

10.0 out of 10, Exceptional, (34)
"My wife and I loved our weekend stay at this cabin!"
The price is HK$2,791
HK$5,484 total
includes taxes & fees
1 Jul - 2 Jul
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Terrace/patio

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

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Mountaintop Horse Farm with Heated Pool
Outdoor pool, a heated pool

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (27)
"This was a much needed haven! Frank was very helpful and hospitable. All of the animals were a definite plus! "
Mountaintop Horse Farm with Heated Pool
Historic cottage in Deep River, CT
Property grounds

Historic cottage in Deep River, CT

10.0 out of 10, Exceptional, (1)
"Wonderful stay. Charming and perfect. "
The price is HK$1,845
HK$3,303 total
includes taxes & fees
20 Jul - 21 Jul
Historic cottage in Deep River, CT
Relax by the River | Branford Waterfront Home
Fridge, microwave, oven, stovetop

Relax by the River | Branford Waterfront Home

8.8 out of 10, Excellent, (3)
"Clean, family friendly, and fun."
Relax by the River | Branford Waterfront Home
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Exterior

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

10.0 out of 10, Exceptional, (61)
"We had an absolute blast and could not have been easier for check in and accommodations very prefect. The place was prefect for our trip w/ beautiful decor and extremely spacious for everyone’s needs. Thank you for a great stay."
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

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"
The price is HK$841
HK$2,029 total
includes taxes & fees
1 Jul - 2 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Cozy apartment in charming Hartford with AC, WiFi
Private kitchen

Cozy apartment in charming Hartford with AC, WiFi

The price is HK$903
HK$1,331 total
includes taxes & fees
13 Jul - 14 Jul
Cozy apartment in charming Hartford with AC, WiFi
Relaxing summer rental, walking distance to the beach, short ride to the outlets
Exterior

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

9.8 out of 10, Exceptional, (47)
"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
The gardners Cottage 1 mile from long Island Sound - pet friendly
Property grounds

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (14)
"Robin was a great resource about the area. Her property was amazing the cottage was fantastic. Very comfortable and clean. We had a relaxing stay and a great time. We would love to go back again and again!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Lux Boutique Large Private LOFT Pratt St Hartford
Iron/ironing board, WiFi, bed sheets

Lux Boutique Large Private LOFT Pratt St Hartford

9.2 out of 10, Wonderful, (16)
"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."
The price is HK$1,327
HK$1,865 total
includes taxes & fees
1 Jul - 2 Jul
Lux Boutique Large Private LOFT Pratt St Hartford
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Dining

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (29)
"The property was perfect for our beach vacation."
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Cozy 2-bedroom apartment in charming West Hartford with WiFi
Fridge, oven, stovetop, coffee/tea maker

Cozy 2-bedroom apartment in charming West Hartford with WiFi

7.0 out of 10, Good, (4)
"The property was very clean, spacious and comfortable. It suited our needs well."
Cozy 2-bedroom apartment in charming West Hartford with WiFi
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Beach nearby, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (45)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Property grounds

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

9.6 out of 10, Exceptional, (7)
"The lake view was amazing. The house was beautiful and the hosts were great."
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (12)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
Blue Back Bungalow
Waterfront Beach House
Terrace/patio

Waterfront Beach House

9.6 out of 10, Exceptional, (44)
"The property is nicely located on the water and convenient to many attractions. "
Waterfront Beach House
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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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 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.