Middletown Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Middletown holiday 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 HK$1,375
HK$2,866 total
includes taxes & fees
17 Jun - 18 Jun
#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 HK$719
HK$1,906 total
includes taxes & fees
10 Jun - 11 Jun
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 HK$1,626
HK$3,484 total
includes taxes & fees
10 Jun - 11 Jun
#29 - Modern 5 Bedroom/2 Bath
Dining

3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
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 HK$1,293
HK$2,246 total
includes taxes & fees
6 Jul - 7 Jul
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 HK$940
HK$2,707 total
includes taxes & fees
10 Jun - 11 Jun
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 HK$1,230
HK$2,762 total
includes taxes & fees
15 Jun - 16 Jun
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)
"I loved the location and the view!"
United States
Gabrielly
The price is HK$1,058
HK$1,577 total
includes taxes & fees
9 Jul - 10 Jul
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
1 bedroom, desk, iron/ironing board, travel cot

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 HK$621
HK$1,402 total
includes taxes & fees
10 Jun - 11 Jun
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 HK$979
HK$3,541 total
includes taxes & fees
10 Jun - 11 Jun
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.
#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 HK$713
HK$1,563 total
includes taxes & fees
29 Jun - 30 Jun
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 HK$1,567
HK$3,507 total
includes taxes & fees
10 Jun - 11 Jun
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 HK$940
HK$1,238 total
includes taxes & fees
17 Jun - 18 Jun
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 HK$1,593
HK$3,539 total
includes taxes & fees
10 Jun - 11 Jun
#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 HK$1,303
HK$3,550 total
includes taxes & fees
10 Jun - 11 Jun
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 HK$1,528
HK$2,458 total
includes taxes & fees
10 Jun - 11 Jun
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 HK$2,172
HK$4,269 total
includes taxes & fees
15 Jun - 16 Jun
#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 HK$1,609
HK$3,606 total
includes taxes & fees
17 Jun - 18 Jun
#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 HK$1,081
HK$1,760 total
includes taxes & fees
1 Jul - 2 Jul
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

8/10 Good
"WiFi didn’t work, as well as main overheard light. A bit transient and seemingly long terms stays"
Chaim 1-night trip
Posted 2 hours ago
Motel 6 Wethersfield, CT - Hartford

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
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Are there holiday rentals in Middletown?

Yes, there are holiday rentals in Middletown close to Van Vleck Observatory, or you can select a more secluded option if you're looking for 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 holiday rentals that Middletown has to offer?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: This holiday home rental outside of Middletown is located in the city centre, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

With 11 Expedia holiday rentals, you're guaranteed 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 holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.