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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is AED 337
AED 875 total
includes taxes & fees
27 Sep - 28 Sep
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, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is AED 582
AED 1,202 total
includes taxes & fees
28 Sep - 29 Sep
#24 Serenity A Lakefront Cottage Retreat
Exterior

3. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (31 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is AED 511
AED 935 total
includes taxes & fees
29 Sep - 30 Sep
Family Stays: Middletown, CT
Dining

4. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is AED 470
AED 1,121 total
includes taxes & fees
28 Sep - 29 Sep
3 BR Apartment Near Wesleyan 201
Smart TV

5. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
The price is AED 804
AED 1,839 total
includes taxes & fees
7 Oct - 8 Oct
#29 - Modern 5 Bedroom/2 Bath
Coffee/tea maker, fridge, microwave, oven

6. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.2 out of 10, Good, (5 reviews)
"Very clean. No frills."
United States
Kristoph
The price is AED 393
AED 1,065 total
includes taxes & fees
28 Sep - 29 Sep
Private Apt in Middletown-Wesleyan 101
Dining

7. 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.
3 BR Apartment Near Wesleyan 202
Exterior

8. 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
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
The price is AED 1,706
AED 2,877 total
includes taxes & fees
30 Sep - 1 Oct
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Exterior

9. 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, (192 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
The price is AED 465
AED 704 total
includes taxes & fees
30 Sep - 1 Oct
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Smart TV, fireplace, books, music library

10. 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, (37 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is AED 466
AED 927 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
TV

11. 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)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is AED 433
AED 1,031 total
includes taxes & fees
5 Oct - 6 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
Interior

12. 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 470
AED 1,070 total
includes taxes & fees
5 Oct - 6 Oct
Private Apartment in Berlin
TV

13. 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 1,031 total
includes taxes & fees
27 Oct - 28 Oct
Newly Remodeled with deck. Close to town center
1 bedroom, iron/ironing board, WiFi, bed sheets

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

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
The price is AED 433
AED 1,031 total
includes taxes & fees
27 Sep - 28 Sep
Once the old Schools house now a newly furnished Apartment
Exterior

15. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is AED 433
AED 1,071 total
includes taxes & fees
12 Oct - 13 Oct
All New 1BR with tons of Charm
Smart TV

16. #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.
The price is AED 634
AED 1,372 total
includes taxes & fees
7 Oct - 8 Oct
#23 COMFORT & LUXURY 3 BR/2 BA House
Iron/ironing board, WiFi, bed sheets

17. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is AED 992
AED 2,223 total
includes taxes & fees
27 Sep - 28 Sep
The Cottage by the Woods -private getaway to relax
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 1,031 total
includes taxes & fees
30 Sep - 1 Oct
All New Private and Cozy in great location
Interior

19. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is AED 253
AED 921 total
includes taxes & fees
7 Oct - 8 Oct
The Sun Filled Cozy Creamery
Interior

20. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (32 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is AED 2,387
AED 3,585 total
includes taxes & fees
27 Sep - 28 Sep
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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

New Haven Hotel

New Haven Hotel

8/10 Good
"The staff members at check-in & check-out were warmly professional and attentive. What a gorgeous & spacious living room area with appealing decor. The breakfast options were fantastic for self-serve options. The room was immaculate. Two points that led me to rate it a 4.7 out of 5 = the extremely hard bed & non-working light & electric fixtures on the side of the bed by the window."
Maria Luisa 1-night trip
Posted 1 hour ago
New Haven Hotel

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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental outside of Middletown is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Artfarm.

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.