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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is HK$800
HK$1,928 total
includes taxes & fees
9 Nov - 10 Nov
2BR Apartment Near Wesleyan 102
Veterans Park, near the house

2. 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 HK$1,176
HK$2,101 total
includes taxes & fees
30 Nov - 1 Dec
Family Stays: Middletown, CT
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

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$800
HK$2,135 total
includes taxes & fees
9 Nov - 10 Nov
Private Apt in Middletown-Wesleyan 101
A wooden deck with a railing, overlooking a calm lake with autumn foliage.

4. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (27 reviews)
"It was great "
United States
Rodrigo C.
#24 *Serenity* A Lakefront Cottage Retreat
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.
The price is HK$1,631
HK$3,696 total
includes taxes & fees
23 Nov - 24 Nov
#29 - Modern 5 Bedroom/2 Bath
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.

6. 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 HK$980
HK$1,973 total
includes taxes & fees
2 Dec - 3 Dec
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A cabin with a dining table set for two, a bicycle, and a small porch area.

7. 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, (218 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is HK$996
HK$1,507 total
includes taxes & fees
7 Dec - 8 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A hotel reception area with a counter, a digital tablet, and a poster on the wall.

8. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Wethersfield
10.0 out of 10, Exceptional, (51 reviews)
"Quick stop, quiet room near the highway."
United States
Anonymous traveller
The price is HK$605
HK$696 total
includes taxes & fees
8 Nov - 9 Nov
1 Queen Bed | Micfridge
Stairwell

9. 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 HK$878
HK$2,044 total
includes taxes & fees
9 Nov - 10 Nov
Private Apartment in Berlin
A hotel reception area with a receptionist, a guest, and a child.

10. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Wethersfield
10.0 out of 10, Exceptional, (49 reviews)
"Simple rooms close to I-91 made travel convenient."
United States
Anonymous traveller
The price is HK$575
HK$661 total
includes taxes & fees
8 Nov - 9 Nov
1 Queen Bed | Smoking
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.

11. 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$1,035
HK$2,280 total
includes taxes & fees
9 Nov - 10 Nov
Newly Remodeled with deck. Close to town center
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

12. 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 HK$1,035
HK$2,280 total
includes taxes & fees
25 Nov - 26 Nov
Fully Furnished 1BR Apartment
A modern kitchen with a central island, bar stools, and pendant lighting.

13. 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 HK$5,683
HK$8,958 total
includes taxes & fees
7 Nov - 8 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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 HK$628
HK$3,676 total
includes taxes & fees
2 Dec - 3 Dec
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
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 HK$1,035
HK$2,334 total
includes taxes & fees
10 Nov - 11 Nov
All New 1BR with tons of Charm
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

16. 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 HK$1,035
HK$2,280 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.

17. 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$1,144
HK$1,884 total
includes taxes & fees
24 Nov - 25 Nov
Walk To Goodspeed Opera House!
A modern living room with a sectional sofa, a coffee table, and a kitchen in the background.

18. #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)
"Perfect for our family stay this past weekend in ct. Close to shopping and restaurants. The house had everything we would of needed to whip together a meal. Beds were comfy and clean."
United States
Lynn O.
#23 *COMFORT & LUXURY* 3 BR/2 BA House
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

19. 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 HK$1,035
HK$2,280 total
includes taxes & fees
19 Nov - 20 Nov
All New Studio apartment in center of town
A modern kitchen with a wooden island, white cabinetry, and a ceiling fan.

20. 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 HK$1,035
HK$2,280 total
includes taxes & fees
17 Nov - 18 Nov
New Railside Residents
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

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"Wonderful stay, clean rooms and great customer service from the staff."
Francesca 2-night trip
Posted 1 hour ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

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 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 Artfarm.

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.