A forested landscape with a winding dirt road and power lines.

Middletown Vacation Rentals

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Middletown vacation rentals

Dining

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
$285 nightly
The price is $323
Jun 30 - Jul 1
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.0 out of 10, Very Good, (1 review)
"Excellent beds and clean."
United States
DANIEL M.
$255 nightly
The price is $289
Jun 29 - Jun 30
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
8.0 out of 10, Very Good, (1 review)
"The apartment is the first floor of a two story duplex. It was very clean and larger than we were expecting. We had just about everything we needed for our stay. We really appreciate being able to bring our pets with us. I enjoyed walking around the neighborhood with my dog."
United States
Douglas M.
$342 nightly
The price is $387
Jun 30 - Jul 1
Total with taxes and fees
3 BR Apartment Near Wesleyan 202
Fridge, microwave, oven, stovetop

Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.4 out of 10, Good, (3 reviews)
"Very clean. No frills."
United States
Kristoph
$280 nightly
The price is $317
Jun 29 - Jun 30
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101
Interior

Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
$287 nightly
The price is $324
Jun 28 - Jun 29
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
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, (8 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
$409 nightly
The price is $462
Jun 28 - Jun 29
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV, books

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.
Old Lyme
$187 nightly
The price is $211
Jun 29 - Jun 30
Total with taxes and fees
Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (139 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
$629 nightly
The price is $712
Jul 1 - Jul 2
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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
Old Saybrook
9.8 out of 10, Exceptional, (38 reviews)
"Enjoyed our stay"
United States
Nicole L.
$1,598 nightly
The price is $1,808
Jul 7 - Jul 8
Total with taxes and fees
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
A lakeside setting with a row of colorful kayaks and a sailboat docked.

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
10.0 out of 10, Exceptional, (156 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
$343 nightly
The price is $388
Jul 26 - Jul 27
Total with taxes and fees
Go Jump in the Lake!
Terrace/patio

Peek-A-Boo View, Amston Lake

Peek-A-Boo View, Amston Lake
Lebanon
9.8 out of 10, Exceptional, (50 reviews)
"Enjoyed our time here, owner available and helpful"
United States
Kathleen C.
$343 nightly
The price is $388
Jun 29 - Jun 30
Total with taxes and fees
Peek-A-Boo View, Amston Lake
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.
$400 nightly
The price is $453
Jun 28 - Jun 29
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Dining

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
$643 nightly
The price is $727
Jul 24 - Jul 25
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
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, (46 reviews)
"We enjoyed our stay"
United States
JM B.
$244 nightly
The price is $276
Jul 1 - Jul 2
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Living area

The Beach Nest-Lux Cottage Steps to the Beach

The Beach Nest-Lux Cottage Steps to the Beach
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
United States
Karol W.
The Beach Nest-Lux Cottage Steps to the Beach
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (38 reviews)
"Needed a one night stay - worked fine"
United States
Michelle B.
$266 nightly
The price is $301
Jun 30 - Jul 1
Total with taxes and fees
Walk To Goodspeed Opera House!
Fridge, microwave, oven, stovetop

The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$443 nightly
The price is $502
Jul 1 - Jul 2
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (160 reviews)
"Great stay! "
United States
Tanitra
$184 nightly
The price is $212
Jul 27 - Jul 28
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Property grounds

NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (5 reviews)
$278 nightly
The price is $315
Jun 30 - Jul 1
Total with taxes and fees
NEW Coastal Cottage 2 Miles to Beach + Lake Access
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.
$314 nightly
The price is $356
Jul 23 - Jul 24
Total with taxes and fees
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Hotel is great! Rooms are spacious & have comfortable beds!"
lynne 2-night trip
Posted 2 hours ago
Holiday Inn Express Southington by IHG

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 $212 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?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: This vacation home rental outside of Middletown is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

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 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.