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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Middletown holiday rentals

A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

1. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
The price is HK$1,107
HK$2,423 total
includes taxes & fees
27 Aug - 28 Aug
2BR Apartment Near Wesleyan 102
A dining room with a rectangular table and four chairs, a window with blinds, a recessed ceiling light, and a wall-mounted air conditioning unit.

2. 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$1,646
HK$3,629 total
includes taxes & fees
31 Aug - 1 Sept
3 BR Apartment Near Wesleyan 202
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

3. “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 HK$1,764
HK$2,271 total
includes taxes & fees
31 Aug - 1 Sept
“3BR Home Near Wesleyan & Downtown Middletown
A modern living room with a sofa, a dining table, and a massage chair.

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 HK$2,508
HK$4,804 total
includes taxes & fees
23 Sept - 24 Sept
#29 - Modern 5 Bedroom/2 Bath
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

5. 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 HK$1,108
HK$2,653 total
includes taxes & fees
27 Aug - 28 Aug
Private Apt in Middletown-Wesleyan 101
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

6. 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 HK$1,426
HK$3,059 total
includes taxes & fees
3 Sept - 4 Sept
3 BR Apartment Near Wesleyan 201
A two-story house with a front porch, a garage, and a well-maintained lawn.

7. 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 HK$3,787
HK$6,669 total
includes taxes & fees
8 Sept - 9 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A cabin with a large window, surrounded by trees.

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, (182 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is HK$992
HK$1,862 total
includes taxes & fees
1 Sept - 2 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

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, (36 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 HK$980
HK$2,022 total
includes taxes & fees
7 Sept - 8 Sept
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern kitchen with a central island, bar stools, and pendant lighting.

10. 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
9.8 out of 10, Exceptional, (30 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 HK$5,094
HK$8,103 total
includes taxes & fees
7 Sept - 8 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

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 HK$807
HK$2,049 total
includes taxes & fees
31 Aug - 1 Sept
Private Apartment in Berlin
A lakeside property with a gazebo, dock, kayaks, and a flag.

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.
Lakeview Carriage House with Spectacular Sunset Views

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

The Cottage by the Woods -private getaway to relax
Meriden
The price is HK$2,116
HK$5,018 total
includes taxes & fees
27 Aug - 28 Aug
The Cottage by the Woods -private getaway to relax
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

14. 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 HK$925
HK$2,318 total
includes taxes & fees
27 Aug - 28 Aug
All New Studio apartment in center of town

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)
"Very nice! Clean and had everything you would need for a few nights away from home. I book again. "
United States
ALRUNDUS L.
The price is HK$925
HK$2,317 total
includes taxes & fees
30 Aug - 31 Aug
All New 1BR with tons of Charm
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

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.
#23 *COMFORT & LUXURY* 3 BR/2 BA House
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

17. 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 HK$925
HK$2,318 total
includes taxes & fees
30 Aug - 31 Aug
Once the old Schools house now a newly furnished Apartment
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

18. 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.
The price is HK$925
HK$2,310 total
includes taxes & fees
20 Sept - 21 Sept
Newly Remodeled 1-BR Close to Everything yet Very Private
A living room with a grey sofa, yellow cushions, a wooden coffee table, a TV on a stand, and a lamp on a side table.

19. 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$925
HK$2,318 total
includes taxes & fees
10 Sept - 11 Sept
Newly Remodeled with deck. Close to town center
A living room with a dark blue sofa, a round ottoman, a coffee table, and a TV on a stand. There is a large abstract painting on the wall and a window with curtains.

20. Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is HK$1,305
HK$3,914 total
includes taxes & fees
8 Sept - 9 Sept
Cozy basement apartment with private bathroom, kitchen and entrance.
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

10/10 Excellent
"The location was perfect and the ability to try different restaurants steps away made it so easy to grab dinner/lunch/coffee last minute. Will defiantly be staying there again!"
Salima 4-night trip
Posted 3 hours ago
New Haven Hotel

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
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • 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 10 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.