Photo by Simmie Reagor

Middletown Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 31 - Nov 2
In two weeks
Nov 7 - Nov 9

Vacation Rentals in Middletown

3 bedrooms, iron/ironing board, WiFi, bed sheets
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
5.4 out of 10, (3)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
United States
Jenn U.
$248 nightly
The price is $281
Nov 3 - Nov 4
Total with taxes and fees
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (76)
"Very nice cabins "
United States
Jairo
$189 nightly
The price is $217
Oct 27 - Oct 28
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Fridge, microwave, oven, stovetop
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
United States
Anonymous traveler
$217 nightly
The price is $246
Oct 27 - Oct 28
Total with taxes and fees
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Totally Private Cozy studio in awesome Hartford with WiFi, AC
8.6 out of 10, Excellent, (11)
"Great!"
United States
Sahai S.
$140 nightly
The price is $158
Oct 27 - Oct 28
Total with taxes and fees
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford
Lux Boutique Large Private LOFT Pratt St Hartford
8.4 out of 10, Very Good, (21)
"Location was great. Lots of things to do and many nearby options for eating and drinks. View was disappointing—dark and one window facing a brick wall. Biggest complaint was neighbors and noise—first two nights there was loud music and parties until early morning hours."
United States
Mike and Jaime R.
$144 nightly
The price is $163
Oct 27 - Oct 28
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Fridge, microwave, oven, stovetop
Private Apartment in Berlin
Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
$279 nightly
The price is $316
Oct 26 - Oct 27
Total with taxes and fees
Private Apartment in Berlin
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (33)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
$155 nightly
The price is $176
Nov 4 - Nov 5
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
10.0 out of 10, Exceptional, (33)
"Very much enjoyed our stay!"
United States
Barb D.
$315 nightly
The price is $357
Oct 29 - Oct 30
Total with taxes and fees
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Exterior
Shoreline Oasis
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"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!"
United States
Julie
$230 nightly
The price is $261
Oct 26 - Oct 27
Total with taxes and fees
Shoreline Oasis
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Waterfront Cottage in Branford
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (97)
"Such a beautiful home and amazing views! Stayed here with friends for a wedding and it was the most ideal. "
United States
Bradie S.
Waterfront Cottage in Branford
Dining
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Exterior
Charming Studio| Near Yale| Downtown New Haven
Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (9)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
$205 nightly
The price is $205
Oct 27 - Oct 28
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Microwave, electric kettle, cookware/dishes/utensils, paper towels
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
9.6 out of 10, Exceptional, (4)
"Cozy, clean, comfortable. Location is excellent and accessible to restaurants and venues. Highly recommended. "
United States
Jason B.
$177 nightly
The price is $200
Nov 1 - Nov 2
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Interior
Conference Room Rental no sleeping arrangements
Conference Room Rental no sleeping arrangements
$823 nightly
The price is $931
Oct 26 - Oct 27
Total with taxes and fees
Conference Room Rental no sleeping arrangements
Private kitchen
Fully Furnished Private Loft Style Charm Trumbull Elevator
Fully Furnished Private Loft Style Charm Trumbull Elevator
7.0 out of 10, Good, (2)
"Great place to stay. Lots of room compared to a hotel room and it's nice to have the kitchen area. We used the bonus spaces a lot and found the building to be very quiet from room to room. The noise from outside at night was mostly car noise and seemed pretty standard for being in a central location. Thank you!"
United States
Emily
$170 nightly
The price is $193
Oct 27 - Oct 28
Total with taxes and fees
Fully Furnished Private Loft Style Charm Trumbull Elevator
Property grounds
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
9.8 out of 10, Exceptional, (6)
"Everything was amazing "
United States
MELISSA G.
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA
Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (2)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
$356 nightly
The price is $403
Nov 3 - Nov 4
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Fridge, microwave, oven, stovetop
New Cozy 2BR Stay New Haven Close to Yale
New Cozy 2BR Stay New Haven Close to Yale
2.0 star property
7.4 out of 10, Good, (3)
"Place was great for family and having a washer and dryer was a big help. Place was super clean and comfortable "
United States
CHUCK C.
$244 nightly
The price is $254
Oct 26 - Oct 27
Total with taxes and fees
New Cozy 2BR Stay New Haven Close to Yale
Exterior
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (50)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
$617 nightly
The price is $698
Nov 3 - Nov 4
Total with taxes and fees
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Dining
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
9.8 out of 10, Exceptional, (70)
"Great family get together where we all were very comfortable. "
United States
Leanne B.
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Great location and very accommodating staff"
Randall 4-night trip
Posted 2 days ago
Omni New Haven Hotel at Yale

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Private Apartment in Berlin: This vacation home rental outside of Middletown is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Middletown?

With 9 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 General Mansfield House.

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.