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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
The price is ￥14,458
￥42,612 total
includes taxes & fees
Oct 29 - Oct 30
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
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is ￥14,458
￥38,313 total
includes taxes & fees
Oct 29 - Oct 30
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.

3. 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.

4. 2BR Apartment Near Wesleyan 303

2BR Apartment Near Wesleyan 303
Washington Street Historic District
The price is ￥22,679
￥53,799 total
includes taxes & fees
Oct 29 - Oct 30
2BR Apartment Near Wesleyan 303
A room with a patterned rug, a door leading to a kitchen, and a window with blinds.

5. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is ￥20,159
￥39,955 total
includes taxes & fees
Nov 3 - Nov 4
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.

6. #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 ￥30,144
￥74,038 total
includes taxes & fees
Nov 3 - Nov 4
#29 - Modern 5 Bedroom/2 Bath
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

7. 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 ￥18,741
￥48,168 total
includes taxes & fees
Nov 18 - Nov 19
Private Apt in Middletown-Wesleyan 101
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

8. 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 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, (39 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 ￥19,686
￥41,380 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A glass enclosure with a view of a forest interior, including a bed and a small table with items.

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, (212 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is ￥23,466
￥34,230 total
includes taxes & fees
Nov 3 - Nov 4
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Stairwell

11. 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 ￥14,458
￥38,675 total
includes taxes & fees
Oct 29 - Oct 30
Private Apartment in Berlin
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

12. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Wethersfield
10.0 out of 10, Exceptional, (51 reviews)
"Towels fresh, no hassle at all throughout my stay here."
United States
Anonymous traveler
The price is ￥11,325
￥13,023 total
includes taxes & fees
Nov 6 - Nov 7
1 Queen Bed | Micfridge
A hotel room with a bed, bedside tables, a microwave, a refrigerator, a toilet, and a shower.

13. 1 Full Bed | Deluxe, Micfridge, Smoking

1 Full Bed | Deluxe, Micfridge, Smoking
Wethersfield
10.0 out of 10, Exceptional, (51 reviews)
"Good value for what you get here. Clean room with a fridge and TV included."
United States
Anonymous traveler
The price is ￥11,172
￥12,847 total
includes taxes & fees
Nov 20 - Nov 21
1 Full Bed | Deluxe, Micfridge, Smoking
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

14. 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 ￥20,789
￥48,791 total
includes taxes & fees
Nov 2 - Nov 3
Once the old Schools house now a newly furnished Apartment
Building

15. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (13 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is ￥20,789
￥48,791 total
includes taxes & fees
Nov 2 - Nov 3
All New 1BR with tons of Charm
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

16. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
The price is ￥20,789
￥48,791 total
includes taxes & fees
Oct 29 - Oct 30
All New Studio apartment in center of town
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

17. 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 ￥20,789
￥48,791 total
includes taxes & fees
Nov 25 - Nov 26
Fully Furnished 1BR Apartment
A large, white, multi-story building with a prominent tower and a flag on top.

18. 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 ￥19,749
￥35,587 total
includes taxes & fees
Nov 24 - Nov 25
Walk To Goodspeed Opera House!
A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

19. New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"Clean & comfortable, in an architecturally unique setting. Great proximity to a variety of downtown shops & restaurants - check out Center Street Brewing Co. for some excellent beer."
United States
Thomas S.
The price is ￥20,789
￥48,791 total
includes taxes & fees
Nov 16 - Nov 17
New Railside Residents
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

20. 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 ￥16,867
￥81,740 total
includes taxes & fees
Oct 29 - Oct 30
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Please do consider driving to the Pizza places not walking specially at Night."
Hien 1-night trip
Posted 3 hours ago
Omni New Haven Hotel at Yale

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 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.