Middletown Holiday Rentals

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Our top choices for Middletown holiday rentals

9.8 out of 10, Exceptional, (21 reviews)
"It was our 3rd time staying and everything was as expected. New updates to the bathroom were nice surprise. Thanks again for a lovely stay while we visited our daughter at Wesleyan. "
United States
Robb F.
#24 *Serenity* A Lakefront Cottage Retreat

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is AU$303
includes taxes & fees
8 Mar - 9 Mar
Cozy Guest Suite in Historic Home

Holiday Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (22 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 AU$315
includes taxes & fees
16 Mar - 17 Mar
Family Stays: Middletown, CT

Holiday Home in Middletown

#29 - Modern 5 Bedroom/2 Bath
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is AU$534
includes taxes & fees
3 Mar - 4 Mar
#29 - Modern 5 Bedroom/2 Bath

Apartment in Washington Street Historic District

2BR Apartment Near Wesleyan 301
The price is AU$379
includes taxes & fees
3 Mar - 4 Mar
2BR Apartment Near Wesleyan 301

Apartment in Washington Street Historic District

2BR Apartment Near Wesleyan 102
The price is AU$379
includes taxes & fees
8 Mar - 9 Mar
2BR Apartment Near Wesleyan 102

Holiday Home in Washington Street Historic District

3-bedroom Unit in tranquil Middletown
7.2 out of 10, Good, (5 reviews)
"Nice place"
United States
Jousette C.
The price is AU$396
includes taxes & fees
3 Mar - 4 Mar
3-bedroom Unit in tranquil Middletown

Apartment in Washington Street Historic District

Private Apt in Middletown-Wesleyan 101
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 AU$399
includes taxes & fees
17 Mar - 18 Mar
Private Apt in Middletown-Wesleyan 101
9.6 out of 10, Exceptional, (121 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 AU$241
includes taxes & fees
3 Mar - 4 Mar
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is AU$549
includes taxes & fees
3 Mar - 4 Mar
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Apartment in East Haddam

Walk To Goodspeed Opera House!
9.4 out of 10, Exceptional, (34 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 AU$444
includes taxes & fees
6 Mar - 7 Mar
Walk To Goodspeed Opera House!
10.0 out of 10, Exceptional, (55 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is AU$1,120
includes taxes & fees
3 Mar - 4 Mar
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
9.8 out of 10, Exceptional, (8 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 AU$475
includes taxes & fees
3 Mar - 4 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$429
includes taxes & fees
3 Mar - 4 Mar
Once the old Schools house now a newly furnished Apartment
9.6 out of 10, Exceptional, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is AU$256
includes taxes & fees
6 Mar - 7 Mar
1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (15 reviews)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is AU$454
includes taxes & fees
3 Mar - 4 Mar
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
10.0 out of 10, Exceptional, (5 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is AU$400
includes taxes & fees
3 Mar - 4 Mar
Modern & Cozy Cape | 4 Bedroom House | Central Location

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AU$429
includes taxes & fees
3 Mar - 4 Mar
All New 1BR with tons of Charm
9.6 out of 10, Exceptional, (19 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is AU$388
includes taxes & fees
9 Mar - 10 Mar
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
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 favourite 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 depend 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 AU$241 per night. Entering your travel dates in the search wizard might find you 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?

A spacious TREETOPS Reunion/ Retreat/Event venue! Sleeps 10-12. Seasonal POOL!: 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 Kidcity Children's Museum and Van Vleck Observatory, 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 Middletown Nature Gardens.

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.