Middletown Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Middletown holiday rentals

Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (19 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is HK$975
HK$1,847 total
includes taxes & fees
2 Feb - 3 Feb
Family Stays: Middletown, CT
Interior

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
2.0 star property
Washington Street Historic District
The price is HK$788
HK$2,330 total
includes taxes & fees
18 Jan - 19 Jan
2BR Apartment Near Wesleyan 301
Interior

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is HK$1,151
HK$1,675 total
includes taxes & fees
15 Jan - 16 Jan
Cozy Guest Suite in Historic Home
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.
The price is HK$866
HK$2,381 total
includes taxes & fees
9 Feb - 10 Feb
Private Apt in Middletown-Wesleyan 101
Smart TV

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Beautiful home and well suited for a peaceful stay. Great neighborhood and a wonderful how. Would recommend the property to anyone."
United States
LaToya O.
The price is HK$1,661
HK$3,673 total
includes taxes & fees
31 Jan - 1 Feb
#29 - Modern 5 Bedroom/2 Bath
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
2.0 star property
Washington Street Historic District
The price is HK$788
HK$2,306 total
includes taxes & fees
18 Jan - 19 Jan
2BR Apartment Near Wesleyan 102
Smart TV

3-bedroom Unit in tranquil Middletown

3-bedroom Unit in tranquil Middletown
Washington Street Historic District
6.6 out of 10, (4 reviews)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
United States
Jenn U.
The price is HK$1,248
HK$1,591 total
includes taxes & fees
21 Jan - 22 Jan
3-bedroom Unit in tranquil Middletown
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, (102 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is HK$723
HK$1,190 total
includes taxes & fees
20 Jan - 21 Jan
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
9.0 out of 10, Wonderful, (12 reviews)
"Great location, exactly as advertised. The shades are somewhat translucent, so a bit bright at night, but wore a mask and it was fine. "
United States
Scott B.
The price is HK$530
HK$1,404 total
includes taxes & fees
15 Jan - 16 Jan
Charming Studio| Near Yale| Downtown New Haven
Interior

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

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is HK$754
HK$2,836 total
includes taxes & fees
15 Jan - 16 Jan
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
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, (5 reviews)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is HK$674
HK$3,126 total
includes taxes & fees
27 Jan - 28 Jan
Rogers Lake House (87) · CT College+Beach+USCGA
Microwave, electric kettle, cookware/dishes/utensils, paper towels

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Downtown Hartford
9.6 out of 10, Exceptional, (5 reviews)
"Great location. Clean property"
United States
Sue R.
The price is HK$780
HK$1,509 total
includes taxes & fees
18 Jan - 19 Jan
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Interior

The Historic Hideaway

The Historic Hideaway
2.0 star property
Avon
7.0 out of 10, Good, (2 reviews)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is HK$429
HK$1,901 total
includes taxes & fees
15 Jan - 16 Jan
The Historic Hideaway
Property grounds

Humble Abode #2

Humble Abode #2
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$936
HK$1,232 total
includes taxes & fees
13 Feb - 14 Feb
Humble Abode #2
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is HK$788
HK$2,299 total
includes taxes & fees
18 Jan - 19 Jan
Private Apartment in Berlin
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, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$679
HK$1,466 total
includes taxes & fees
20 Jan - 21 Jan
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, computer monitors

Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is HK$673
HK$1,640 total
includes taxes & fees
3 Feb - 4 Feb
Central Chic Pad - with Free Parking, Heat & AC
Fridge, microwave, oven, stovetop

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is HK$741
HK$1,591 total
includes taxes & fees
19 Jan - 20 Jan
One bedroom apartment in United States of America, New Haven
Iron/ironing board, WiFi, bed sheets

Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
Downtown Hartford
8.6 out of 10, Excellent, (26 reviews)
"Great stay"
United States
Josh H.
The price is HK$780
HK$1,188 total
includes taxes & fees
15 Jan - 16 Jan
Lux Boutique Large Private LOFT Pratt St Hartford
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$1,064
HK$3,909 total
includes taxes & fees
20 Jan - 21 Jan
Beachside Bliss w/ Game Room, Gym & Golf Green
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"Great staff. Clean, comfortable room."
Charlotte 1-night trip
Posted 20 hours ago
Hampton Inn & Suites Hartford/East 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 Kidcity Children's Museum, 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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of Middletown offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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 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 General Mansfield House.

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.