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Middletown Holiday Rentals

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Our top choices for Middletown holiday rentals

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is NZ$371
includes taxes & fees
3 Jan - 4 Jan
Cozy Guest Suite in Historic Home

Holiday Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (19)
"The location worked well for our needs. The house was super clean. The host supplied everything that you would hope to have and then went above and beyond.Would not hesitate to stay again. Thanks Gilbert for a wonderful stay!"
United States
ronald c.
The price is NZ$411
includes taxes & fees
7 Jan - 8 Jan
Family Stays: Middletown, CT

Apartment in Washington Street Historic District

Apartment in Middletown-Wesleyan 102
2.0 star property
The price is NZ$516
includes taxes & fees
4 Jan - 5 Jan
Apartment in Middletown-Wesleyan 102
9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
#24 *Serenity* A Lakefront Cottage Retreat

Holiday Home in Middletown

#29 - Modern 5 Bedroom/2 Bath
9.4 out of 10, Exceptional, (6)
"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.
#29 - Modern 5 Bedroom/2 Bath

Holiday Home in Washington Street Historic District

3-bedroom Unit in tranquil Middletown
6.6 out of 10, (4)
"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 NZ$425
includes taxes & fees
8 Jan - 9 Jan
3-bedroom Unit in tranquil Middletown

Apartment in Washington Street Historic District

Private Apt in Middletown-Wesleyan 101
6.0 out of 10, (2)
"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 NZ$519
includes taxes & fees
6 Jan - 7 Jan
Private Apt in Middletown-Wesleyan 101
9.6 out of 10, Exceptional, (96)
"Place was beautiful. If I had any questions I was able to text and they responded back so quickly. "
United States
Lee
The price is NZ$280
includes taxes & fees
22 Jan - 23 Jan
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is NZ$317
includes taxes & fees
10 Jan - 11 Jan
1-bedroom cottage with Grove Beach 🏖️ access.
10.0 out of 10, Exceptional, (6)
"Place is nice would stay again "
United States
nic
The price is NZ$642
includes taxes & fees
18 Jan - 19 Jan
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
10.0 out of 10, Exceptional, (5)
"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 NZ$698
includes taxes & fees
4 Jan - 5 Jan
Rogers Lake House (87) · CT College+Beach+USCGA

Apartment in West Hartford

The Blue Back Bungalow
2.0 star property
9.4 out of 10, Exceptional, (18)
"The stay was good. The house is located in a great area and very close to my family member we were visiting. I will stay again and make sure everything is in order. "
United States
Vanessia P.
The Blue Back Bungalow

Apartment in Manchester Center

Humble Abode #2
2.0 star property
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
The price is NZ$273
includes taxes & fees
3 Jan - 4 Jan
Humble Abode #2
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is NZ$498
includes taxes & fees
2 Jan - 3 Jan
Once the old Schools house now a newly furnished Apartment
9.4 out of 10, Exceptional, (14)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is NZ$284
includes taxes & fees
14 Jan - 15 Jan
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is NZ$358
includes taxes & fees
26 Jan - 27 Jan
Central Chic Pad - with Free Parking, Heat & AC

Holiday Home in Plainville

#26 Beautifully Renovated 2 BR Home
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is NZ$404
includes taxes & fees
5 Jan - 6 Jan
#26 Beautifully Renovated 2 BR Home
10.0 out of 10, Exceptional, (6)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is NZ$346
includes taxes & fees
4 Jan - 5 Jan
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2)
"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 NZ$421
includes taxes & fees
9 Jan - 10 Jan
The Historic Hideaway
2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$763
includes taxes & fees
5 Jan - 6 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

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middletown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as NZ$263 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday 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 holiday.

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. 

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.