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Middletown Vacation Rentals

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In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Middletown vacation rentals

Exterior
Family Stays: Middletown, CT

Vacation Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (19 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
$209 nightly
The price is $237
Feb 2 - Feb 3
Total with taxes and fees
Family Stays: Middletown, CT
Interior
2BR Apartment Near Wesleyan 301

Apartment in Washington Street Historic District

2BR Apartment Near Wesleyan 301
2.0 star property
$264 nightly
The price is $299
Jan 13 - Jan 14
Total with taxes and fees
2BR Apartment Near Wesleyan 301
Interior
Cozy Guest Suite in Historic Home

Vacation Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
$190 nightly
The price is $215
Jan 13 - Jan 14
Total with taxes and fees
Cozy Guest Suite in Historic Home
Fridge, microwave, oven, stovetop
Private Apt in Middletown-Wesleyan 101

Apartment in Washington Street Historic District

Private Apt in Middletown-Wesleyan 101
6.0 out of 10, (2 reviews)
"The apartment was exactly what we needed to rest between events at Wesleyan. Good communication, fixed an air conditioner and added one prior to our arrival (and it was very very hot. So it was appreciated."
United States
Carolyn O.
$273 nightly
The price is $310
Feb 9 - Feb 10
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101
Smart TV
#29 - Modern 5 Bedroom/2 Bath

Vacation Home in Middletown

#29 - Modern 5 Bedroom/2 Bath
9.4 out of 10, Exceptional, (6 reviews)
"Beautiful home and well suited for a peaceful stay. Great neighborhood and a wonderful how. Would recommend the property to anyone."
United States
LaToya O.
$438 nightly
The price is $470
Jan 31 - Feb 1
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath
Dining
2BR Apartment Near Wesleyan 102

Apartment in Washington Street Historic District

2BR Apartment Near Wesleyan 102
2.0 star property
$213 nightly
The price is $241
Jan 13 - Jan 14
Total with taxes and fees
2BR Apartment Near Wesleyan 102
Smart TV
3-bedroom Unit in tranquil Middletown

Vacation Home in Washington Street Historic District

3-bedroom Unit in tranquil Middletown
6.6 out of 10, (4 reviews)
"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.
$214 nightly
The price is $243
Jan 19 - Jan 20
Total with taxes and fees
3-bedroom Unit in tranquil Middletown
View from property
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cabin in East Haddam

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (101 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
$149 nightly
The price is $171
Jan 13 - Jan 14
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior
Charming Studio| Near Yale| Downtown New Haven

Apartment in Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (12 reviews)
"Great location, exactly as advertised. The shades are somewhat translucent, so a bit bright at night, but wore a mask and it was fine. "
United States
Scott B.
$170 nightly
The price is $170
Jan 14 - Jan 15
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Interior
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Vacation Home in Salem

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
$322 nightly
The price is $363
Jan 13 - Jan 14
Total with taxes and fees
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Smart TV, books
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5 reviews)
"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.
$354 nightly
The price is $401
Jan 13 - Jan 14
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Microwave, electric kettle, cookware/dishes/utensils, paper towels
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Apartment in Downtown Hartford

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
9.6 out of 10, Exceptional, (5 reviews)
"Great location. Clean property"
United States
Sue R.
$170 nightly
The price is $193
Jan 13 - Jan 14
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Interior
The Historic Hideaway

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2 reviews)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
$232 nightly
The price is $244
Jan 13 - Jan 14
Total with taxes and fees
The Historic Hideaway
Property grounds
Humble Abode #2

Apartment in Manchester Center

Humble Abode #2
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
$140 nightly
The price is $158
Jan 13 - Jan 14
Total with taxes and fees
Humble Abode #2
Interior
Private Apartment in Berlin

Vacation Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
$261 nightly
The price is $296
Jan 13 - Jan 14
Total with taxes and fees
Private Apartment in Berlin
1 bedroom, desk, iron/ironing board, travel crib
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$157 nightly
The price is $178
Jan 23 - Jan 24
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC

Apartment in Manchester

Central Chic Pad - with Free Parking, Heat & AC
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
$196 nightly
The price is $209
Jan 13 - Jan 14
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
Fridge, microwave, oven, stovetop
One bedroom apartment in United States of America, New Haven

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
9.4 out of 10, Exceptional, (3 reviews)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
$180 nightly
The price is $204
Jan 13 - Jan 14
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Apartment in Downtown Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
8.6 out of 10, Excellent, (26 reviews)
"Great stay"
United States
Josh H.
$135 nightly
The price is $152
Jan 13 - Jan 14
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
$451 nightly
The price is $511
Jan 20 - Jan 21
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
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

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Excellent service start to finish "
Garrett 1-night trip
Posted 13 hours ago
Hampton Inn & Suites Hartford/Farmington

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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This vacation home rental outside of Middletown offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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 Connecticut River and Wadsworth Falls State Park 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.