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Middletown Vacation Rentals

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Check prices for these dates

Tonight
Jul 4 - Jul 5
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Jul 5 - Jul 6
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

Vacation Rentals in Middletown

Postcard Cabins Machimoodus
Standard Cabin, 1 Queen Bed | Exterior

Postcard Cabins Machimoodus

2.0 star property
9.8 out of 10, Exceptional, (31)
"Great stay"
The price is CA $216
CA $303 total
includes taxes & fees
Jul 9 - Jul 10
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 CA $243
CA $358 total
includes taxes & fees
Jul 6 - Jul 7
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 CA $537
CA $1,008 total
includes taxes & fees
Jul 13 - Jul 14
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.
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 CA $165
CA $372 total
includes taxes & fees
Jul 6 - Jul 7
1-bedroom cottage with Grove Beach 🏖️ access.
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 CA $299
CA $546 total
includes taxes & fees
Jul 22 - Jul 23
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, (60)
"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
Cozy apartment in charming Hartford with AC, WiFi
Private kitchen

Cozy apartment in charming Hartford with AC, WiFi

The price is CA $156
CA $230 total
includes taxes & fees
Jul 13 - Jul 14
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
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
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 CA $189
CA $268 total
includes taxes & fees
Aug 1 - Aug 2
Lux Boutique Large Private LOFT Pratt St Hartford
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
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room
Game room

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

The price is CA $208
CA $410 total
includes taxes & fees
Jul 6 - Jul 7
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room
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)
"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.
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 "
The price is CA $136
CA $478 total
includes taxes & fees
Jul 22 - Jul 23
Blue Back Bungalow
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 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 11 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 Connecticut Valley Railroad State Park Trail.

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.