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

Middletown Holiday 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 holiday rentals

Property grounds

1. #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 HK$1,251
HK$2,693 total
includes taxes & fees
28 Sept - 29 Sept
#24 Serenity A Lakefront Cottage Retreat
Exterior

2. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (30 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is HK$981
HK$1,826 total
includes taxes & fees
12 Oct - 13 Oct
Family Stays: Middletown, CT
Coffee/tea maker, fridge, microwave, oven

3. 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 HK$1,004
HK$2,488 total
includes taxes & fees
23 Sept - 24 Sept
Private Apt in Middletown-Wesleyan 101
Dining

4. 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 HK$1,090
HK$2,898 total
includes taxes & fees
22 Sept - 23 Sept
3 BR Apartment Near Wesleyan 202
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 HK$1,503
HK$3,689 total
includes taxes & fees
23 Sept - 24 Sept
#29 - Modern 5 Bedroom/2 Bath
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
9.6 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 HK$3,678
HK$6,531 total
includes taxes & fees
5 Oct - 6 Oct
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Dining

7. 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 HK$1,028
HK$2,515 total
includes taxes & fees
29 Sept - 30 Sept
3 BR Apartment Near Wesleyan 201
Desk, laptop workspace, bed sheets

8. 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, (191 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is HK$1,012
HK$1,525 total
includes taxes & fees
22 Sept - 23 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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, (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 HK$1,051
HK$2,097 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Interior

10. 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 HK$1,075
HK$2,381 total
includes taxes & fees
13 Oct - 14 Oct
Private Apartment in Berlin
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 HK$926
HK$2,288 total
includes taxes & fees
22 Sept - 23 Sept
Newly Remodeled 1-BR Close to Everything yet Very Private
TV

12. 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 HK$926
HK$2,288 total
includes taxes & fees
22 Sept - 23 Sept
Newly Remodeled with deck. Close to town center
1 bedroom, iron/ironing board, WiFi, bed sheets

13. 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)
"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 HK$926
HK$2,288 total
includes taxes & fees
22 Sept - 23 Sept
Once the old Schools house now a newly furnished Apartment
Coffee/tea maker, fridge, microwave, oven

14. All New Fully Furnished Cozy Studio

All New Fully Furnished Cozy Studio
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Clean and well designed apartment in a great location. Book here if you are interested as you won't have any regrets. Enjoy! "
United States
Rick C.
The price is HK$926
HK$2,288 total
includes taxes & fees
22 Sept - 23 Sept
All New Fully Furnished Cozy Studio
Exterior

15. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveller
The price is HK$1,341
HK$2,221 total
includes taxes & fees
4 Oct - 5 Oct
Walk To Goodspeed Opera House!
TV

16. 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 HK$926
HK$2,226 total
includes taxes & fees
30 Sept - 1 Oct
All New Private and Cozy in great location
Interior

17. 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 HK$541
HK$1,967 total
includes taxes & fees
22 Sept - 23 Sept
The Sun Filled Cozy Creamery
Interior

18. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is HK$1,373
HK$2,462 total
includes taxes & fees
22 Sept - 23 Sept
Bristol Condo Near Espn HQ & Lake Compounce!
Smart TV, offices, computer monitors

19. 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$677
HK$1,680 total
includes taxes & fees
27 Sept - 28 Sept
Central Chic Pad - with Free Parking, Heat & AC
Iron/ironing board, WiFi, bed sheets

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is HK$2,118
HK$5,023 total
includes taxes & fees
22 Sept - 23 Sept
The Cottage by the Woods -private getaway to relax
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

Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

10/10 Excellent
"The property was very clean. Very well kept"
Eugene T 4-night trip
Posted 5 hours ago
Best Western Plus New England Inn & Suites

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
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  • 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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Middletown is located on the beach, and has a balcony, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Middletown?

With 9 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 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 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.