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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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.
$271 nightly
The price is $307
Oct 14 - Oct 15
Total with taxes and fees
2BR Apartment Near Wesleyan 301
A bedroom with a bed, a radiator, a dresser, and two windows with blinds.

2. 2BR Apartment Near Wesleyan 303

2BR Apartment Near Wesleyan 303
Washington Street Historic District
$320 nightly
The price is $404
Oct 13 - Oct 14
Total with taxes and fees
2BR Apartment Near Wesleyan 303
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

3. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
$215 nightly
The price is $243
Oct 13 - Oct 14
Total with taxes and fees
2BR Apartment Near Wesleyan 102
Veterans Park, near the house

4. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (33 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
$226 nightly
The price is $256
Oct 14 - Oct 15
Total with taxes and fees
Family Stays: Middletown, CT
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

5. 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.
$255 nightly
The price is $289
Oct 14 - Oct 15
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
A bedroom with a bed, two bedside tables, a nightstand, and two wall-mounted artworks.

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.
$423 nightly
The price is $449
Oct 13 - Oct 14
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

7. “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.
$254 nightly
The price is $288
Oct 31 - Nov 1
Total with taxes and fees
“3BR Home Near Wesleyan & Downtown Middletown
A two-story house with a front porch, a garage, and a well-maintained lawn.

8. 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.
$717 nightly
The price is $811
Oct 13 - Oct 14
Total with taxes and fees
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

9. 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
$260 nightly
The price is $294
Oct 14 - Oct 15
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101
A cabin with a dining table set for two, a bicycle, and a small porch area.

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, (201 reviews)
"Great experience and the perfect environment"
United States
Stephanie
$167 nightly
The price is $192
Nov 11 - Nov 12
Total with taxes and fees
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.

11. 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, (38 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.
$227 nightly
The price is $257
Oct 19 - Oct 20
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Stairwell

12. 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.
$217 nightly
The price is $246
Oct 13 - Oct 14
Total with taxes and fees
Private Apartment in Berlin
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, (34 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.
$913 nightly
The price is $1,033
Oct 13 - Oct 14
Total with taxes and fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

14. 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, (11 reviews)
"We really liked this property! Modernized apartment in an older home. Clean, comfortable, and close to family in the area. Karl was great to work with. We will stay here again next time we visit family!"
United States
Alan
$274 nightly
The price is $292
Oct 13 - Oct 14
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

15. 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
$274 nightly
The price is $292
Oct 13 - Oct 14
Total with taxes and fees
Fully Furnished 1BR Apartment
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
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$274 nightly
The price is $292
Oct 13 - Oct 14
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

17. 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.
$277 nightly
The price is $295
Oct 16 - Oct 17
Total with taxes and fees
All New Studio apartment in center of town
Building

18. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (12 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
$274 nightly
The price is $292
Oct 13 - Oct 14
Total with taxes and fees
All New 1BR with tons of Charm
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

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

The Cottage by the Woods -private getaway to relax
Meriden
$566 nightly
The price is $640
Oct 13 - Oct 14
Total with taxes and fees
The Cottage by the Woods -private getaway to relax
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.

20. 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.
$274 nightly
The price is $292
Oct 27 - Oct 28
Total with taxes and fees
Newly Remodeled with deck. Close to town center
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

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

8/10 Good
"The same breakfast for three days and the last day they have only bagels. The coffee machine out of order."
jose 3-night trip
Posted 3 hours ago
Clarion Inn North Haven - New Haven North

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $192 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.