Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Middletown vacation rentals

Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
$336 nightly
The price is $362
May 31 - Jun 1
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
$228 nightly
The price is $258
Jun 1 - Jun 2
Total with taxes and fees
2BR Apartment Near Wesleyan 102
Dining

3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
$320 nightly
The price is $362
May 31 - Jun 1
Total with taxes and fees
3 BR Apartment Near Wesleyan 202
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (27 reviews)
"The property was clean and welcoming. The hosts included many special touches. Would definitely stay again. "
United States
Michelle P.
$245 nightly
The price is $278
Jun 16 - Jun 17
Total with taxes and fees
Family Stays: Middletown, CT
Smart TV

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
$426 nightly
The price is $458
Jun 10 - Jun 11
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath
Dining

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
$336 nightly
The price is $381
Jun 9 - Jun 10
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
Fridge, microwave, oven, stovetop

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
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.
$271 nightly
The price is $307
Jun 1 - Jun 2
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101
1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (42 reviews)
"Extremely cozy, comfortable and clean! Really impressed after walking through the door...details of flowers, fruit, water, and coffee and tea. Pleasantly Surprised and would definitely stay again and recommend. Thank you!!"
United States
Kristen B.
$192 nightly
The price is $217
May 31 - Jun 1
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (154 reviews)
"I loved the location and the view!"
United States
Gabrielly
$175 nightly
The price is $201
Jun 29 - Jun 30
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
10.0 out of 10, Exceptional, (154 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
$297 nightly
The price is $336
May 31 - Jun 1
Total with taxes and fees
Go Jump in the Lake!
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.6 out of 10, Exceptional, (37 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
$242 nightly
The price is $274
Jun 4 - Jun 5
Total with taxes and fees
Walk To Goodspeed Opera House!
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
$406 nightly
The price is $459
Jun 3 - Jun 4
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (2 reviews)
"the place was clean bed was nice"
United States
Jonathan
$140 nightly
The price is $158
May 31 - Jun 1
Total with taxes and fees
Humble Abode #2
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$357 nightly
The price is $404
May 31 - Jun 1
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Property grounds

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$275 nightly
The price is $312
Jun 4 - Jun 5
Total with taxes and fees
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$272 nightly
The price is $290
Jun 1 - Jun 2
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Interior

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
9.8 out of 10, Exceptional, (10 reviews)
"Place is nice would stay again "
United States
nic
$382 nightly
The price is $431
Jun 1 - Jun 2
Total with taxes and fees
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
$106 nightly
The price is $119
Jun 7 - Jun 8
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
Cookware/dishes/utensils

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.6 out of 10, Exceptional, (15 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveler
$293 nightly
The price is $307
Jun 3 - Jun 4
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Interior

Modern Studio Retreat

Modern Studio Retreat
Dwight
$222 nightly
The price is $231
Jun 19 - Jun 20
Total with taxes and fees
Modern Studio Retreat
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

Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

6/10 Okay
"NO WIFI!! IT SUCKED!! WIFI WAS DOWN THROUGH OUT MY STAY!!!"
Joseph 2-night trip
Posted 10 hours ago
Motel 6 Wethersfield, CT - Hartford

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 $201 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?

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!: This vacation home rental outside of Middletown offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Middletown?

With 10 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 Artfarm.

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.