Bright colors of autumn. View above. Road in the forest. Middletown, Connecticut

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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.
The price is ￥28,105
￥58,587 total
includes taxes & fees
Jun 16 - Jun 17
#24 *Serenity* A Lakefront Cottage Retreat
Shower, towels, shampoo

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.
The price is ￥14,703
￥38,962 total
includes taxes & fees
Jun 11 - Jun 12
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.
The price is ￥33,246
￥71,226 total
includes taxes & fees
Jun 10 - Jun 11
#29 - Modern 5 Bedroom/2 Bath
Dining

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
The price is ￥27,387
￥59,523 total
includes taxes & fees
Jun 11 - Jun 12
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.
The price is ￥26,426
￥45,925 total
includes taxes & fees
Jul 6 - Jul 7
Family Stays: Middletown, CT
Shower, towels, shampoo

3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
The price is ￥25,465
￥63,319 total
includes taxes & fees
Jun 15 - Jun 16
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.
The price is ￥24,825
￥56,256 total
includes taxes & fees
Jun 16 - Jun 17
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, (156 reviews)
"Great stay! "
United States
Tanitra
The price is ￥25,465
￥36,651 total
includes taxes & fees
Jun 16 - Jun 17
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, (44 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
The price is ￥12,685
￥28,658 total
includes taxes & fees
Jun 10 - Jun 11
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, (7 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is ￥23,944
￥77,518 total
includes taxes & fees
Jun 14 - Jun 15
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.
The price is ￥39,244
￥74,599 total
includes taxes & fees
Jun 30 - Jul 1
#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.
The price is ￥12,172
￥29,173 total
includes taxes & fees
Jun 15 - Jun 16
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.
The price is ￥32,032
￥71,672 total
includes taxes & fees
Jun 10 - Jun 11
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
The price is ￥19,219
￥25,305 total
includes taxes & fees
Jun 10 - Jun 11
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.
The price is ￥31,875
￥71,410 total
includes taxes & fees
Jun 10 - Jun 11
#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
The price is ￥23,324
￥68,318 total
includes taxes & fees
Jun 10 - Jun 11
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.
The price is ￥23,223
￥39,920 total
includes taxes & fees
Jun 10 - Jun 11
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.
The price is ￥44,385
￥87,239 total
includes taxes & fees
Jun 15 - Jun 16
#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.
The price is ￥32,561
￥73,162 total
includes taxes & fees
Jun 15 - Jun 16
#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.
The price is ￥21,622
￥35,596 total
includes taxes & fees
Jun 23 - Jun 24
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

The Farmington Inn & Suites

The Farmington Inn & Suites

10/10 Excellent
"A completely excellent hotel. I would live here. Staff A+. Room A+. Cleaning A+ Reception and its quirky but professional amenities A+ It is even in the 'town centre' so local shops etc are on your door step. The pure luck of finding this place was luck indeed."
Alexander 1-night trip
Posted 3 hours ago
The Farmington Inn & Suites

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
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Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Are there vacation rentals in Middletown?

Yes, you can find vacation rentals in Middletown close to Van Vleck Observatory, 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 Van Vleck Observatory and Kidcity Children's Museum, whereas Connecticut River and General Mansfield House 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.