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Middletown Vacation Rentals

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In two weeks
Oct 24 - Oct 26
In one month
Nov 7 - Nov 9
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4

Vacation Rentals in Middletown

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
3 bedrooms, iron/ironing board, WiFi, bed sheets

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."
$248 nightly
The price is $281
Oct 20 - Oct 21
Total with taxes and fees
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.0 star property
9.6 out of 10, Exceptional, (72)
"Very nice cabins "
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Shoreline Oasis
Exterior

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!"
$232 nightly
The price is $263
Oct 13 - Oct 14
Total with taxes and fees
Shoreline Oasis
Lux Boutique Large Private LOFT Pratt St Hartford
Iron/ironing board, WiFi, bed sheets

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."
$144 nightly
The price is $163
Oct 13 - Oct 14
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Totally Private Cozy studio in awesome Hartford with WiFi, AC
WiFi, bed sheets

Totally Private Cozy studio in awesome Hartford with WiFi, AC

8.6 out of 10, Excellent, (11)
"Great!"
$140 nightly
The price is $158
Oct 13 - Oct 14
Total with taxes and fees
Totally Private Cozy studio in awesome Hartford with WiFi, AC
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
Fridge, microwave, oven, stovetop

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!"
$235 nightly
The price is $266
Oct 21 - Oct 22
Total with taxes and fees
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
Cozy apartment in charming Hartford with AC, WiFi
Microwave

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (3)
"All was as advertised. The Xfinity INDOOR theatre us across the the street. Xfinity OUTDOOR theatre/ arena is only about a .8 mile walk away. We took an UBER there and walked back after our concert"
$154 nightly
The price is $174
Oct 13 - Oct 14
Total with taxes and fees
Cozy apartment in charming Hartford with AC, WiFi
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

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. "
$279 nightly
The price is $316
Oct 13 - Oct 14
Total with taxes and fees
Private Apartment in Berlin
Charming Studio| Near Yale| Downtown New Haven
Exterior

Charming Studio| Near Yale| Downtown New Haven

8.6 out of 10, Excellent, (7)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
$213 nightly
The price is $213
Oct 13 - Oct 14
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
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

10.0 out of 10, Exceptional, (33)
"Enjoyed our stay"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Exterior

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

10.0 out of 10, Exceptional, (48)
"Amazing property, we loved everything about it, highly recommended, will stay again "
$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
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Microwave, electric kettle, cookware/dishes/utensils, paper towels

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. "
$178 nightly
The price is $201
Nov 1 - Nov 2
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Experience Downtown Hartford near XL Center
Interior

Experience Downtown Hartford near XL Center

6.0 out of 10, (6)
"The day I arrived the property wasn’t ready and I had to find a hotel near there. Needless to say it’s not near nice areas but that’s where the hotel was. They only told me after I didn’t get a code to get in and I had to contact them. Good news was that they reimbursed the hotel quickly. The unit is very clean but very minimal. The refrigerator has no freezer section and the kitchen only a range top, no oven. There’s also no coffee maker, iron or ironing board and laundry was done offsite. All...
$135 nightly
The price is $152
Oct 13 - Oct 14
Total with taxes and fees
Experience Downtown Hartford near XL Center
Conference Room Rental no sleeping arrangements
Interior

Conference Room Rental no sleeping arrangements

$820 nightly
The price is $928
Oct 13 - Oct 14
Total with taxes and fees
Conference Room Rental no sleeping arrangements
Waterfront House with picture-perfect views from all 3 levels.
Interior

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

9.6 out of 10, Exceptional, (93)
"Took our four grandsons here for a week and it was perfect. Location is great and the house worked perfectly for us. Owners could not be easier to work with "
Waterfront House with picture-perfect views from all 3 levels.
Large Charming Historic House close to Beaches
Fridge, microwave, oven, dishwasher

Large Charming Historic House close to Beaches

9.8 out of 10, Exceptional, (32)
"Great place and location. There was 8 of us and plenty of space and beds!"
Large Charming Historic House close to Beaches
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.4 out of 10, Exceptional, (32)
"Loved the overall stay and experience. The private beach access is a bonus"
$168 nightly
The price is $190
Oct 27 - Oct 28
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Cozy dog friendly updated house in quiet village adjacent to park
Property grounds

Cozy dog friendly updated house in quiet village adjacent to park

10.0 out of 10, Exceptional, (41)
"Comfortable with all the amenities you could need "
Cozy dog friendly updated house in quiet village adjacent to park
Stylish Downtown Business| Hospital | WD | GYM
TV

Stylish Downtown Business| Hospital | WD | GYM

8.6 out of 10, Excellent, (4)
"Central to everything in downtown Hartford! "
$230 nightly
The price is $261
Oct 16 - Oct 17
Total with taxes and fees
Stylish Downtown Business| Hospital | WD | GYM
New Cozy 2BR Stay New Haven Close to Yale
Fridge, microwave, oven, stovetop

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 "
$253 nightly
The price is $263
Oct 13 - Oct 14
Total with taxes and fees
New Cozy 2BR Stay New Haven Close to Yale
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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Friendly staff, very clean and the bed was great. We had the king deluxe room. I’ve never stayed in a big fancy hotel like that before so it was a little overwhelming but I got through it. Would stay there again if I ever came back to the area. "
Michelle 1-night trip
Posted 12 hours 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 $152 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.