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Search Holiday Rentals in Middletown

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May 1 - May 2
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May 2 - May 3
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May 3 - May 5
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May 10 - May 12

Top Holiday Rentals in Middletown

Private kitchen
Cozy newly remodeled home close to major amenities in Connecticut a
9.0 out of 10, Wonderful, (9)
"We stayed here while visiting our family. The property was clean, quiet and exactly as described. The kitchen seemed well stocked. The huge washing machine/dryer was great after our cross country drive. There are just a few things to be aware of: the bathroom is on the second floor. The bed we slept on was not too too comfortable (a little firm for our tastes). The single bed was very firm. Other than that it was a nice place to stay."
Cozy newly remodeled home close to major amenities in Connecticut a
Property grounds
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
9.0 out of 10, Wonderful, (2)
"What a great place! Location, location. Located on edge of Little Italy with great restaurants and bars. Our favorite was Zenellis. Less than 15 minute walk to downtown New Haven with lots of dining options. Take in the Trinity Bar nearby- great fun! Furniture was modest but adequate. Great kitchen."
The price is £255
includes taxes & fees
6 May - 7 May
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Property grounds
Waterfront Beach House
9.6 out of 10, Exceptional, (33)
"The cottage is a perfect cozy stay on the water - we stayed in the winter and still were able to enjoy the sand and the sunrises right outside the window. House is well-appointed and well-located within area with access to restaurants and shops in Clinton, Madison, Westbrook, Old Saybrook, etc."
Waterfront Beach House
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Beach nearby, sun-loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (88)
"Positive experience, great location, and cozy accommodations for a centrally located family weekend."
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Smart TV, fireplace
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
Aerial view
Cozy Escape - Stunning Waterfront Home!
9.8 out of 10, Exceptional, (27)
"This property is truly special. Tucked back in a very quiet and private neighborhood, and right on the ocean with a private beach. The property is well taken care of, very dog friendly, tastefully decorated, modern yet charming, and spotlessly clean. We are quite picky and no matter where we looked, everything was perfectly clean and well kept, truly impressive for a dog friendly property. We would definitely stay here again without hesitation."
Cozy Escape - Stunning Waterfront Home!
Property grounds
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, (50)
"We needed another house to accommodate family in town for a family reunion. It worked about perfectly! And the banana bread was delicious ❤️"
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Private kitchen | Fridge, microwave, oven, stovetop
Beautiful cozy rooms near hospital and down town area
8.4 out of 10, Very good, (9)
"My friends and I had a great time. Nice and spacious. Thanks for quick reaponces."
The price is £199
includes taxes & fees
9 May - 10 May
Beautiful cozy rooms near hospital and down town area
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (110)
"I stayed at this amazing studio cottage with my girlfriend for 2 nights for her birthday. Our hosts, Liz and Adam were simply amazing. They allowed us an early check in and a late check out. Liz even brought out bicycles for us to use to tour around the neighborhood and ride along the shore line. Because it was my girlfriends birthday (or maybe they just do this), they had Prosecco and Orange Juice plus beer and cheese and other snacks for us when we arrived. The cottage is adorable, perfect...
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Microwave, oven, stovetop, dishwasher
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
10.0 out of 10, Exceptional, (2)
"My family and I enjoyed our stay here. We had lots of space for my 4yo to run around and each of my 3 kids had their own room. The house was very clean and the host was easily able to contact if I had questions or concerns. We would def. stay here again"
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
4 bedrooms, iron/ironing board, WiFi, bed sheets
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (79)
"I mean, that view! Photos are accurate and Dave was a great, responsive host. Twelve thumbs up from our group!"
Waterfront Cottage in Branford
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (46)
"We enjoyed our stay for the weekend. We had 2 adults and 2 teenagers. Everyone had room to spread out. There is a full flight of stairs to enter the house and a sunroom that would be nice to enjoy in better weather. Thank you for a nice stay!"
Fun Downtown Location
Beach nearby, sun-loungers, beach towels
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (69)
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, beach towels
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, (38)
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
View from property
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
9.8 out of 10, Exceptional, (22)
"Property exactly as described. What an amazing view and right on the beach. Great communication with host. Answered all our questions very promptly. Would definitely recommend."
The price is £967
includes taxes & fees
24 May - 25 May
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Fridge, microwave, oven, stovetop
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
9.8 out of 10, Exceptional, (55)
"Everything was perfect!! House is amazing for family/friends gathering. Spacious, clean and great views. The home was everything we needed to celebrate the holiday. Thank you to host for communication and special touches throughout the home. Highly recommend"
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
Pool
lakefront estate
3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Interior
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, (8)
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
The price is £192
includes taxes & fees
5 May - 6 May
Shalom Cottage with private beach rights.
Beach | On the beach
DIRECT WATERFRONT PRIVATE BEACH
9.4 out of 10, Exceptional, (22)
"This house is close to the ocean — as in at high tide water is almost to the porch — so very convenient and not a lot of walking needed. Also near to some great restaurants although not walking distance. Owner was friendly and helpful. Only downside is that neighbors are very close (but there is a good privacy fence for the porch) and there are two flights of narrow stairs to get to apartment. We had a relaxing and restorative friends weekend."
DIRECT WATERFRONT PRIVATE BEACH
Exterior
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (57)
"Great cottage with nice amenities. The patio was excellent and the area was very quiet."
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
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See all available properties in Middletown
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.

Other types of properties in Middletown you may be interested in

Front of property – evening/night
Inn at Middletown
3.5 star property
9.0 out of 10, Wonderful, (366)
"Great"
The price is £212
includes taxes & fees
6 May - 7 May
Inn at Middletown
Exterior detail
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1230)
"Nice and clean hotel with friendly and helpful staff. "
The price is £146
includes taxes & fees
13 May - 14 May
New Haven Hotel
Lobby
Best Western Hartford Hotel & Suites
2.5 star property
8.0 out of 10, Very good, (1000)
"The staff was exceptional"
The price is £93
includes taxes & fees
20 May - 21 May
Best Western Hartford Hotel & Suites
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.

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middletown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as £192 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday 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 holiday.

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. 

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?

Patchogue River Retreat, 8 minute walk to West Beach: This holiday home rental outside of Middletown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

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 Harbor Park and Wadsworth Falls State Park are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and Connecticut River.

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.

Recent reviews of Middletown properties
Expedia verified reviews

New Haven Hotel

New Haven Hotel

5/5 Excellent
"Nice and clean hotel with friendly and helpful staff. "
A verified traveller stayed at New Haven Hotel
Posted 2 days ago
New Haven Hotel