A forested landscape with a winding dirt road and power lines.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Middletown vacation rentals

Dining

1. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (4 reviews)
"Excellent beds and clean."
United States
DANIEL M.
2BR Apartment Near Wesleyan 102
Property grounds

2. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
The price is AED 782
AED 1,535 total
includes taxes & fees
18 Aug - 19 Aug
#24 *Serenity* A Lakefront Cottage Retreat
Dining

3. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (1 review)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is AED 768
AED 1,562 total
includes taxes & fees
9 Sep - 10 Sep
3 BR Apartment Near Wesleyan 201
Smart TV

4. #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 AED 1,136
AED 2,188 total
includes taxes & fees
19 Aug - 20 Aug
#29 - Modern 5 Bedroom/2 Bath
Coffee/tea maker, fridge, microwave, oven

5. “3BR Home Near Wesleyan & Downtown Middletown

“3BR Home Near Wesleyan & Downtown Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
The price is AED 918
AED 1,188 total
includes taxes & fees
9 Sep - 10 Sep
“3BR Home Near Wesleyan & Downtown Middletown
Exterior

6. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.8 out of 10, Exceptional, (17 reviews)
"Large, comfortable house in a tranquil part of town. "
United States
Daryl R.
The price is AED 1,994
AED 3,407 total
includes taxes & fees
9 Sep - 10 Sep
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Coffee/tea maker, fridge, microwave, oven

7. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.0 out of 10, Good, (4 reviews)
"Very clean. No frills."
United States
Kristoph
The price is AED 639
AED 1,396 total
includes taxes & fees
9 Sep - 10 Sep
Private Apt in Middletown-Wesleyan 101
Dining

8. 3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
8.0 out of 10, Very Good, (1 review)
"The apartment is the first floor of a two story duplex. It was very clean and larger than we were expecting. We had just about everything we needed for our stay. We really appreciate being able to bring our pets with us. I enjoyed walking around the neighborhood with my dog."
United States
Douglas M.
The price is AED 804
AED 1,731 total
includes taxes & fees
15 Aug - 16 Aug
3 BR Apartment Near Wesleyan 202
Smart TV, fireplace, books, music library

9. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (35 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is AED 459
AED 948 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
View from property

10. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (177 reviews)
"Beautiful view, very clean !"
United States
Karolyne
The price is AED 496
AED 908 total
includes taxes & fees
9 Sep - 10 Sep
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Interior

11. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is AED 569
AED 1,206 total
includes taxes & fees
9 Sep - 10 Sep
Private Apartment in Berlin
Property grounds

12. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is AED 529
AED 1,145 total
includes taxes & fees
3 Sep - 4 Sep
Lakeview Carriage House with Spectacular Sunset Views
TV

13. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
Newly Remodeled 1-BR Close to Everything yet Very Private
Exterior

14. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AED 433
AED 1,068 total
includes taxes & fees
3 Sep - 4 Sep
All New 1BR with tons of Charm
Coffee/tea maker, fridge, microwave, oven

15. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
The price is AED 433
AED 1,068 total
includes taxes & fees
6 Sep - 7 Sep
Fully Furnished 1BR Apartment
1 bedroom, iron/ironing board, WiFi, bed sheets

16. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AED 433
AED 1,068 total
includes taxes & fees
4 Sep - 5 Sep
Once the old Schools house now a newly furnished Apartment
TV

17. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is AED 433
AED 1,082 total
includes taxes & fees
6 Sep - 7 Sep
Newly Remodeled with deck. Close to town center
TV

18. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is AED 433
AED 1,071 total
includes taxes & fees
12 Aug - 13 Aug
All New Private and Cozy in great location
Exterior

19. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is AED 433
AED 1,071 total
includes taxes & fees
26 Aug - 27 Aug
All New Studio apartment in center of town
Coffee/tea maker, fridge, microwave, oven

20. #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, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is AED 979
AED 2,000 total
includes taxes & fees
11 Aug - 12 Aug
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
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

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

8/10 Good
"Very clean and friendly staff"
Kevin 1-night trip
Posted less than an hour ago
Courtyard by Marriott Waterbury Downtown

Frequently asked questions

Are there vacation rentals in Middletown?

Yes, you can find vacation rentals in Middletown close to Kidcity Children's Museum, 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?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: This vacation home rental outside of Middletown is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals are there in Middletown?

With 9 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 Kidcity Children's Museum and Van Vleck Observatory, whereas General Mansfield House and Connecticut River 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 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.