Compare Middletown Vacation Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Middletown Rentals

Postcard Cabins Machimoodus

Postcard Cabins Machimoodus

2 out of 5
298 E Haddam Moodus Rd, East Haddam, CT
10.96 mi from city center
$194 nightly
The price is $223 total per night
$223 total
Jul 9 - Jul 10
Total includes taxes and fees
If you plan to drive, free parking is available. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls.
Kitchen
Pet friendly
Cozy apartment in charming Hartford with AC, WiFi

Cozy apartment in charming Hartford with AC, WiFi

14.22 mi from city center
$150 nightly
The price is $170 total per night
$170 total
Jul 13 - Jul 14
Total includes taxes and fees
At this apartment, guests have access to features like laundry facilities.
Washer
Dryer
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

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

16.61 mi from city center
$657 nightly
The price is $744 total per night
$744 total
Jul 10 - Jul 11
Total includes taxes and fees
At COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎, guests have access to an arcade/game room, laundry facilities, and barbecue grills.
Kitchen
Washer
Historic cottage in Deep River, CT

Historic cottage in Deep River, CT

17.98 mi from city center
$355 nightly
The price is $402 total per night
$402 total
Jul 22 - Jul 23
Total includes taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Air conditioning
Shoreline Oasis

Shoreline Oasis

20.67 mi from city center
$233 nightly
The price is $264 total per night
$264 total
Jul 6 - Jul 7
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
Mountaintop Horse Farm with Heated Pool

Mountaintop Horse Farm with Heated Pool

20.04 mi from city center
At this vacation home, guests have access to an outdoor pool, local meal delivery service, and a water dispenser. This smoke-free vacation home also has a garden.
Pool
Kitchen
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

21.64 mi from city center
$242 nightly
The price is $274 total per night
$274 total
Jul 6 - Jul 7
Total includes taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Air conditioning
Relax by the River | Branford Waterfront Home

Relax by the River | Branford Waterfront Home

21.75 mi from city center
At this vacation home, guests have access to a garden.
Kitchen
Pet friendly
Relaxing summer rental, walking distance to the beach, short ride to the outlets

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

22.06 mi from city center
At this vacation home, guests have access to barbecue grills.
Kitchen
Air conditioning
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

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

22.3 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

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

22.35 mi from city center
At this vacation home, guests have access to an arcade/game room, local meal delivery service, and barbecue grills. Staff members can help with accommodation requests, and provide concierge services. This family-friendly vacation home also has a garden.
Kitchen
Outdoor Space
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

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

23.06 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and local meal delivery service. Other amenities at this beach vacation home include a garden and barbecue grills.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Middletown
View all properties
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.

Middletown Large Group Rentals

How to Book Vacation Rentals in Middletown



🏠 What is the best price for Middletown vacation rentals?

Middletown vacation rentals range in price, starting at $170 per night.


🏠 What types of vacation rentals in Middletown can I rent?

Orbitz offers a wide range of Middletown rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Middletown condo rentals.


🏠 Is it free to cancel my Middletown vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Middletown vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Middletown. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Middletown?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Middletown apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Middletown?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Middletown package deals will get you even more savings.

More Places To Stay in Middletown

Recommended Vacation Rental Locations