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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (165)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (6)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

9.2 out of 10, Wonderful, (5)
The price is AU$964
includes taxes & fees
29 July - 30 July
Charming 2-bedroom cabin close to Fair Hill on horse farm

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 AU$287
includes taxes & fees
27 July - 28 July
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.

9.4 out of 10, Exceptional, (28)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (164)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

10.0 out of 10, Exceptional, (1)
"Very serene and relaxing safe environment "
Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (53)
"I loved the property. The cottage was super clean, tidy and extremely relaxing. Super close to the water, & the views were spectacular. I went for the serenity to fly my drone and capture some great footage. And I certainly was not disappointed . Chris made the check in super easy, with great communication. I absolutely will return. 10 out of 10 rating."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"Great place for a quick getaway - enough room for our family of 4 plus a dog to stay comfortably. Beautiful views! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

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

10.0 out of 10, Exceptional, (5)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (9)
"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 AU$472
includes taxes & fees
28 July - 29 July
Private townhouse near downtown and state park

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
The price is AU$429
includes taxes & fees
27 July - 28 July
Historic Chesapeake City Stay

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is AU$353
includes taxes & fees
10 Aug - 11 Aug
Nature's Haven Tiny Home

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (8)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

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

2.0 star property
9.6 out of 10, Exceptional, (5)
"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 AU$247
includes taxes & fees
12 Aug - 13 Aug
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (268)
"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "
Captivating Chesapeake experience

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is AU$237
includes taxes & fees
27 July - 28 July
Summer Rustic Camping with AC and King Bed

Walk to Town & River: Charming Home in North East!

10.0 out of 10, Exceptional, (2)
"Great stay and responsive host. So definitely stay again. "
Walk to Town & River: Charming Home in North East!

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (54)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
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

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals in Middletown close to Frightland, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Middletown has to offer?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Middletown is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 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 selection of games.

How many holiday rentals are there in Middletown?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What can I see and do in Middletown?

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

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips.