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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Cozy newly remodeled home close to major amenities in Connecticut a
Private kitchen
Cozy newly remodeled home close to major amenities in Connecticut a
8.4 out of 10, Very Good, 10 reviews
"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
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, 113 reviews
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Patchogue River Retreat, 8 minute walk to West Beach
Smart TV, fireplace
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, 6 reviews
"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
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Fun Downtown Location 2nd flr
Dining
Fun Downtown Location 2nd flr
9.8 out of 10, Exceptional, 51 reviews
"Great property for our family trip. We had lots of fun. Owner was responsive and communicative. Hope to be back some day!"
Fun Downtown Location 2nd flr
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
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 reviews
"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 ￥23,341
￥49,434 total
includes taxes & fees
Jun 23 - Jun 24
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Go Jump in the Lake!
Go Jump in the Lake!
10.0 out of 10, Exceptional, 127 reviews
"House was very clean, well equipped and had everything we needed to enjoy a relaxing getaway as a family. We enjoyed the firepit, covered porch and lakeside fun."
The price is ￥32,331
￥56,776 total
includes taxes & fees
Jun 23 - Jun 24
Go Jump in the Lake!
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Aerial view
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, 8 reviews
"We were there for a family event in Glastonbury for just a couple of days, and so we didn't go to the lake. However, the cottage was perfect for our needs -- quiet, allowed for contemplation, and privacy that we needed. We hope to perhaps and experience the beautiful lake."
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Waterfront Cottage in Branford
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, 81 reviews
"Beautiful house in a beautiful location! We hope to return soon!"
Waterfront Cottage in Branford
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
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 reviews
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
The price is ￥71,037
￥129,643 total
includes taxes & fees
Jul 14 - Jul 15
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Beach nearby, beach towels
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, 38 reviews
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
gorgeous victorian direct ocean front single family six bedroom, ten rooms
On the beach, beach towels
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, 51 reviews
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Shalom Cottage with private beach rights.
Interior
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, 8 reviews
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
The price is ￥28,230
￥45,515 total
includes taxes & fees
Jun 20 - Jun 21
Shalom Cottage with private beach rights.
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Smart TV, books, stereo
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
10.0 out of 10, Exceptional, 16 reviews
"My month-long stay was absolutely wonderful. Hunter was an amazing, proactive host. The weather wasn't cooperative in the beginning of my stay, but Hunter went above and beyond to make sure whatever issues arose were taken care of and I couldn't be happier to have made this choice. I will definitely be back!"
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, 89 reviews
"Mel and her husband were awesome! Perfect beach home and location was perfect. House was immaculate! I will stay there again. I only needed to use the first floor and did not have to use the stairs. Very close to the beach. Thank you, Mel!"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Guilford Carriage House at Granite Lodge!
1 bedroom, desk, iron/ironing board, internet
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, 4 reviews
"Gorgeous cottage, spotless, tastefully decorated, thoughtful personal touches, many windows looking into private woods, comfortable bed with beautiful bedding!"
Guilford Carriage House at Granite Lodge!
Beautiful cozy rooms near hospital and down town area
Private kitchen | Fridge, microwave, oven, stovetop
Beautiful cozy rooms near hospital and down town area
8.0 out of 10, Very Good, 11 reviews
"People were very nice and welcoming. Area looks questionable but the place itself is very comfortable, clean and enjoyable."
The price is ￥17,190
￥39,127 total
includes taxes & fees
Jun 27 - Jun 28
Beautiful cozy rooms near hospital and down town area
New Haven Oasis: Steps to Yale & Fine Dining
4 bedrooms, iron/ironing board, bed sheets
New Haven Oasis: Steps to Yale & Fine Dining
10.0 out of 10, Exceptional, 3 reviews
"Was perfect for my family of 8 for the few days we were in New Haven for my PA graduation. Close to all main dining ! Host was very responsive on all questions I had !"
The price is ￥37,886
￥87,849 total
includes taxes & fees
Jun 26 - Jun 27
New Haven Oasis: Steps to Yale & Fine Dining
Cozy Westbrook Vacation Rental - Walk to Beach!
Exterior
Cozy Westbrook Vacation Rental - Walk to Beach!
10.0 out of 10, Exceptional, 3 reviews
"Everything one would need for a beach vacation. Responsive contact person."
Cozy Westbrook Vacation Rental - Walk to Beach!
Amazing Lakefront Property
Smart TV, fireplace, offices
Amazing Lakefront Property
10.0 out of 10, Exceptional, 15 reviews
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Exterior
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, 107 reviews
"A number of friends and I stayed here to be nearby our friends wake and memorial service. It was a really nice homely, quiet space that had plenty of room for everyone and the view over the river is gorgeous. Would love to come back sometime for more uplifting circumstances"
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Don't see what you're looking for?
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

Inn at Middletown
Front of property - evening/night
Inn at Middletown
3.5 star property
9.0 out of 10, Wonderful, 382 reviews
"You go to bathroom and give me the hotel was lovely but the parking was very hard to figure out property needs to update parking needs for people that staying at the hotel."
The price is ￥31,794
￥39,717 total
includes taxes & fees
Jun 25 - Jun 26
Inn at Middletown
New Haven Hotel
Exterior detail
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, 1,249 reviews
"We are visiting Yale. The location of the hotel is good -- walkable to the campus and business around. The room is clean and renovated."
The price is ￥23,499
￥27,024 total
includes taxes & fees
Jun 23 - Jun 24
New Haven Hotel
Best Western Hartford Hotel & Suites
Lobby
Best Western Hartford Hotel & Suites
2.5 star property
7.8 out of 10, Good, 1,001 reviews
"Check-in and check-out were quick and efficient. Beds were comfortable. Breakfast was good. However, at the pool, it was posted that there cannot be drinks, food, and smoking. When my family went to swim on Sunday evening, there was a large crowd of people at the pool and they were playing loud music, smoking, drinking, and eating. "
The price is ￥14,626
￥16,820 total
includes taxes & fees
Jun 26 - Jun 27
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.

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
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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?

Patchogue River Retreat, 8 minute walk to West Beach: This vacation home rental outside of Middletown is located on a river and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals are there in Middletown?

With 8 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 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 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.

Recent reviews of Middletown properties
Expedia verified reviews

New Haven Hotel

New Haven Hotel

5/5 Excellent
"We are visiting Yale. The location of the hotel is good -- walkable to the campus and business around. The room is clean and renovated."
A verified traveler stayed at New Haven Hotel
Posted 1 day ago
New Haven Hotel