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Middletown Vacation Rentals

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Check prices for these dates

Tonight
Jun 21 - Jun 22
Tomorrow
Jun 22 - Jun 23
Next weekend
Jun 27 - Jun 29
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Jul 4 - Jul 6

Vacation Rentals in Middletown

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (261)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (50)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

Charming 2-bedroom cabin close to Fair Hill on horse farm

The price is ￥34,623
￥52,496 total
includes taxes & fees
Jun 24 - Jun 25
Charming 2-bedroom cabin close to Fair Hill on horse farm
Chesapeake Romantic Waterfront Home with Private Pool
Fireplace

Chesapeake Romantic Waterfront Home with Private Pool

9.0 out of 10, Wonderful, (6)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (19)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (174)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Fridge, microwave, oven, stovetop

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

8.8 out of 10, Excellent, (5)
"Was in Wilmington to work a trade show at the Chase Center on the Riverfront. Everything was as described and the communications with the host were great. Only about a 12 minute drive to the venue and lots of restaurants within a 10 minute drive. It’s nothing fancy but for about the same price as a budget hotel room you get a kitchen, two comfy bedrooms and a living room. "
The price is ￥19,059
￥30,975 total
includes taxes & fees
Jun 23 - Jun 24
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Smart TV, fireplace, music library

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.6 out of 10, Exceptional, (24)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Terrace/patio

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"My friends and I wanted a relaxing getaway with beautiful views and that is exactly what we got. Sue was so wonderful and when there was a massive snowstorm expected to come on our arrival date, she offered to change the dates to accommodate us. Everything was wonderful and we had the best stay."
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (40)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
Fridge, microwave, oven, stovetop

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

9.8 out of 10, Exceptional, (87)
"In the area for a wedding. This was a great place for the family to gather in between events. Communication with the owners is top notch. We highly recommend it. "
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is ￥47,202
￥89,058 total
includes taxes & fees
Jul 1 - Jul 2
5-bedroom vacation home 5 minutes from historic Charlestown
Nature's Haven Tiny Home
Terrace/patio

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is ￥27,498
￥34,119 total
includes taxes & fees
Jun 22 - Jun 23
Nature's Haven Tiny Home
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Property grounds

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.4 out of 10, Exceptional, (46)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

2.0 out of 10, (1)
"Never heard from host. Expedia had to cancel reservation."
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Outdoor dining

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (56)
"Great place. Accurately depicted in photos. Nice quiet neighborhood. Super dog friendly!"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (1)
"My family and I had the best time at the Outrange. The house is super cool. But the access to hiking, kayaking and even goats made it perfect. Ben is super good at communication. He responded to any of my questions quickly. I can't say enough about it. Just a really lovely property. "
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Private townhouse near downtown and state park
2 bedrooms, WiFi

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (8)
"The house is clean and comfortable with many amenities and within walking distance of parks and restaurants and museums. The host was very easy to connect with."
The price is ￥23,438
￥44,570 total
includes taxes & fees
Jun 23 - Jun 24
Private townhouse near downtown and state park
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (160)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Iron/ironing board, WiFi, bed sheets

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

2.0 star property
9.0 out of 10, Wonderful, (2)
"We loved the place! It’s adorable and well appointed with necessities. My only complaint (and the reason I gave four stars rather than five) is the bed. I would recommend the owners invest in an actual bed with a comfortable mattress. The sofa bed is not comfortable for sleeping. Otherwise it’s a great little place in a beautiful location, and the owners are very accommodating."
The price is ￥17,459
￥23,442 total
includes taxes & fees
Jun 22 - Jun 23
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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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Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, you can find vacation rentals in Middletown close to Frightland, or you can choose a secluded option if you're looking for extra privacy while you relax. Our travelers say Middletown has a good selection of restaurants. Make sure you have time to check out the festivals and churches during your trip.

What are some of the best vacation rentals that Middletown has to offer?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This vacation home rental near Middletown is located on a lake and has a patio, a garden, 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 hot tub.

How many vacation rentals are there in Middletown?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What can I see and do in Middletown?

Cultural attractions include Everett Theatre and The Everett Annex, whereas Frightland is just one of the family-friendly sights. While here, Middletown Town Hall and Middletown Historic District are other places worth a visit.

What are vacation rentals like in Middletown?

Vacation rentals are private accommodations you can stay in for several days or more in Middletown. Vacation rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.