Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

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.
$352 nightly
The price is $380
Jun 16 - Jun 17
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Shower, towels, shampoo

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
$240 nightly
The price is $272
Jun 8 - Jun 9
Total with taxes and fees
2BR Apartment Near Wesleyan 102
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.
$438 nightly
The price is $470
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
$330 nightly
The price is $374
Jun 11 - Jun 12
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (28 reviews)
"House is immaculate and the hosts were great! Made is feel very welcome. Would definitely stay again!"
United States
Diana C.
$252 nightly
The price is $286
Jul 6 - Jul 7
Total with taxes and fees
Family Stays: Middletown, CT
Shower, towels, shampoo

3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
$302 nightly
The price is $342
Jun 8 - Jun 9
Total with taxes and fees
3 BR Apartment Near Wesleyan 202
Shower, towels, shampoo

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.
$255 nightly
The price is $289
Jun 8 - Jun 9
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101
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, (155 reviews)
"Great stay! "
United States
Tanitra
$175 nightly
The price is $201
Jul 7 - Jul 8
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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, (43 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
$207 nightly
The price is $235
Jun 7 - Jun 8
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
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
$396 nightly
The price is $448
Jun 8 - Jun 9
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV

#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
$347 nightly
The price is $373
Jun 8 - Jun 9
Total with taxes and fees
#23 *COMFORT & LUXURY* 3 BR/2 BA House
1 bedroom, desk, iron/ironing board, WiFi

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
$179 nightly
The price is $203
Jun 29 - Jun 30
Total with taxes and fees
One bedroom in United States of America, New Haven
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
$400 nightly
The price is $453
Jun 9 - Jun 10
Total with taxes and fees
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (3 reviews)
"the place was clean bed was nice"
United States
Jonathan
$140 nightly
The price is $158
Jun 7 - Jun 8
Total with taxes and fees
Humble Abode #2
Bathroom

#43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
8.0 out of 10, Very Good, (1 review)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
$429 nightly
The price is $460
Jun 9 - Jun 10
Total with taxes and fees
#43- Modern Luxury Log Cabin Retreat | Fire Pit
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
$399 nightly
The price is $450
Jun 9 - Jun 10
Total with taxes and fees
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
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.
$214 nightly
The price is $242
Jun 9 - Jun 10
Total with taxes and fees
Walk To Goodspeed Opera House!
Fridge, microwave, oven, stovetop

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
$535 nightly
The price is $579
Jun 15 - Jun 16
Total with taxes and fees
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Fridge, microwave, oven, stovetop

#27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
$425 nightly
The price is $456
Jun 8 - Jun 9
Total with taxes and fees
#27- Luxury Collection
Smart TV

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
$184 nightly
The price is $209
Jun 29 - Jun 30
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2/10 Terrible
"The only recommendation I can leave is don't stay there. At check in, the guy was behind glass and wearing a mask. Ok. But I couldn't understand a thing he said. The tub in room #1 appeared to have been painted once and was chipped all over. The mat in the tub looked moldy. Room #2 lacked the chips, the mat was too similar to the previous one. I wore flip flops to shower...the water that wouldn't drain was still in the tub when I left. Gross. I didn't see a point in dragging my things, cat inckeded, to another room. Walls were dirty but the bed was clean. I do appreciate the absence of a likely questionable bedspread. I did not appreciate what they thought passed as pillows. I booked a non smoking room and as I passed doors with "no smoking" signs to smoke outside, my need for nicotine was markedly decreased. There was active and plentiful smoking behind those doors. Worse than I expected by far."
Judith 6-night trip
Posted 1 hour ago
Motel 6 New Haven - Branford, CT

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?

🌾Welcoming Tiny Home! Downtown & Beachy☀️: This vacation home rental outside of Middletown is located next to a golf course and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 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 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.