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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Middletown vacation rentals

A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

1. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
2BR Apartment Near Wesleyan 301
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

2. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (8 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is AED 337
AED 857 total
includes taxes & fees
11 Nov - 12 Nov
2BR Apartment Near Wesleyan 102
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

3. 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.
3 BR Apartment Near Wesleyan 201
A room with a patterned rug, a door leading to a kitchen, and a window with blinds.

4. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is AED 496
AED 925 total
includes taxes & fees
16 Nov - 17 Nov
Family Stays: Middletown, CT
A modern living room with a leather sofa, a dining table with chairs, a kitchen area with white cabinets, and a chandelier.

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.
#29 - Modern 5 Bedroom/2 Bath
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

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
Private Apt in Middletown-Wesleyan 101
A dining area with a table and chairs, a window with blinds, and a radiator.

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
A spacious living room with a sectional sofa, a coffee table, and a dartboard on the wall.

8. 2BR Apartment Near Wesleyan 303

2BR Apartment Near Wesleyan 303
Washington Street Historic District
2BR Apartment Near Wesleyan 303
A glass enclosure with a view of a forest interior, including a bed and a small table with items.

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, (222 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is AED 466
AED 705 total
includes taxes & fees
9 Dec - 10 Dec
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.

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, (40 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 459
AED 928 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

11. 1 Queen Bed | Wethersfield

1 Queen Bed | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Quick check-in and quiet room helped us get good rest before hitting the road again."
United States
Anonymous traveler
The price is AED 269
AED 309 total
includes taxes & fees
11 Nov - 12 Nov
1 Queen Bed | Wethersfield
Stairwell

12. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
8.8 out of 10, Excellent, (8 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is AED 347
AED 877 total
includes taxes & fees
11 Nov - 12 Nov
Private Apartment in Berlin
A hotel room with a neatly made bed, a bedside table with a lamp, and a window with patterned curtains.

13. 2 Full Beds | Wethersfield

2 Full Beds | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (52 reviews)
"My short stopover went well, beds were supportive but not too firm, setting remained calm despite being next to interstate."
United States
Anonymous traveler
The price is AED 287
AED 330 total
includes taxes & fees
11 Nov - 12 Nov
2 Full Beds | Wethersfield
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

14. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is AED 294
AED 1,715 total
includes taxes & fees
20 Nov - 21 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A modern kitchen with a central island, bar stools, and pendant lighting.

15. 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, (35 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 2,663
AED 4,058 total
includes taxes & fees
10 Dec - 11 Dec
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

16. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (4 reviews)
"This property was very clean and comfortable; a nicely remodeled apartment in an older home. We had family members staying in one of the other apartments, so it was great to have them so close, but still had privacy. The location is conveniently located with plenty of restaurants nearby, and a short drive to fowntown dining and shops. Karl was an excellent host, griendly and very responsive. Would definitely stay here again!"
United States
Ryan
The price is AED 485
AED 1,064 total
includes taxes & fees
25 Nov - 26 Nov
Fully Furnished 1BR Apartment
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.

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 485
AED 1,090 total
includes taxes & fees
11 Nov - 12 Nov
Newly Remodeled with deck. Close to town center
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

18. Brand New Platform #1

Brand New Platform #1
Wallingford Center
9.6 out of 10, Exceptional, (4 reviews)
"This is the second time we have stayed at this location, although it was a different "platform/room." Once again, a very nice stay. Room was perfect for the 2 of us, and all the right ameneties. This is a perfect location within Wallenford, with access to everything, whether walking or driving. The property is very well maintained, and feels very secure. "
United States
Cherie G.
The price is AED 485
AED 1,090 total
includes taxes & fees
11 Nov - 12 Nov
Brand New Platform #1
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

19. 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, (16 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AED 485
AED 1,050 total
includes taxes & fees
12 Nov - 13 Nov
Once the old Schools house now a newly furnished Apartment
A large, white, multi-story building with a prominent tower and a flag on top.

20. 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 traveler
The price is AED 716
AED 1,105 total
includes taxes & fees
15 Nov - 16 Nov
Walk To Goodspeed Opera House!
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

Economy Inn

Economy Inn

8/10 Good
"I am not sure but it seems like this hotel has new management. If not, then the old owners finally gave the place a makeover."
Joseph 1-night trip
Posted 3 hours ago
Economy Inn

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.