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Middletown Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Middletown Vacation Homes

Chesapeake Bay House with Dock & Private Beach
Relax on the lakeside deck with a round table and four Adirondack chairs, surrounded by a rocky shoreline and a wooden pier.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Nancy’s Touch, A Waterfront Paradise!
Stroll through the serene garden, featuring a picturesque arborway, vibrant flowers, and a birdhouse, surrounded by a tranquil body of water.

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (165)
"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
Relax by the pool surrounded by lush greenery and comfortable wicker furniture.

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
Private townhouse near downtown and state park
Cozy retreat with a comfortable bed, desk, and TV, offering a peaceful atmosphere.

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 CA $222
CA $419 total
includes taxes & fees
Aug 7 - Aug 8
Private townhouse near downtown and state park
Ultimate Retreat @ Papermill Rd
Equipped with a microwave, oven, and dishwasher, this kitchen offers a window for natural light and a clean, contemporary design.

Ultimate Retreat @ Papermill Rd

9.2 out of 10, Wonderful, (7)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Relax in this stylish living space with a flat-screen TV and comfortable couch.

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

9.8 out of 10, Exceptional, (18)
"We rented this townhouse for a month for my son's surgical residency rotation at Cristiana Care. It was a perfect location and easy to get to and from the hospital. Owner was very responsive with any questions / concerns which we appreciated. Very quiet and close to grocery stores. Even had a Trader Joe's close by!"
The price is CA $291
CA $488 total
includes taxes & fees
Aug 6 - Aug 7
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Enjoy meals at the central island with a round table and two chairs in this well-equipped kitchen.

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Enjoy a serene beach experience with access to the ocean via the public pier.

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

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Captivating Chesapeake experience
Relax on the pier with a view of distant landforms.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (269)
"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
Walk to Town & River: Charming Home in North East!
Fridge, microwave, stovetop, dishwasher

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!
Charming 3-bedroom lake house with a seasonal private pool and seasonal hot tub!
Cozy retreat with a large bed, bedside table, and window view.

Charming 3-bedroom lake house with a seasonal private pool and seasonal hot tub!

10.0 out of 10, Exceptional, (3)
"Exceptional rental. So many spots to gather with friends. Pool was clean and refreshing. The landscape was gorgeous. The lake was tranquil. The kitchen was well stocked with everything we needed. Seven women wanting a peaceful retreat. Your home exceeded our expectations. Thank you for having us!"
Charming 3-bedroom lake house with a seasonal private pool and seasonal hot tub!
Luxury 2-bedroom house with Water views, Chesapeake City
Enjoy a scenic view of the lake from this kitchen, featuring a large window and stainless steel appliances.

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (2)
"This is a gorgeous property with a great water view of the canalThe house is beautifully decorated and comfortable, and we loved the upper deck. We had a few issues and Gwen addressed them quickly. The restaurants in town are great and in walking distance. There are interesting areas nearby to explore. "
Luxury 2-bedroom house with Water views, Chesapeake City
3 Mi to Dtwn: Home w/ Yard in Newark
Enjoy cooking in this well-equipped kitchen with a stainless steel oven, microwave, and sink.

3 Mi to Dtwn: Home w/ Yard in Newark

9.6 out of 10, Exceptional, (8)
"We loved staying here, location is great!"
3 Mi to Dtwn: Home w/ Yard in Newark
Wilmington Comfort 4 Min to Riverfront fenced yard
Kitchen features a refrigerator, oven, and microwave, with a window offering a view.

Wilmington Comfort 4 Min to Riverfront fenced yard

9.2 out of 10, Wonderful, (20)
"Good location in downtown Wilmington that works well for a small group looking for a good alternative to nearby Riverfront hotels. "
Wilmington Comfort 4 Min to Riverfront fenced yard
Waterfront house with amazing views. Top of the Chesapeake
Relax on the deck with Adirondack chairs and enjoy the serene lake view.

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (99)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Simple, two-story building with a flat roof, surrounded by trees in a tranquil setting.

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

10.0 out of 10, Exceptional, (55)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Modern kitchen with white cabinetry, black stove, and microwave.

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Tip Of The Town Fresh and New 3 Bedroom Nest
Modern kitchen with white cabinetry, stainless steel appliances, and a large window.

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (23)
"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
Stay & Play at Our Beautiful Retreat
Surrounded by lush trees, this pool offers a serene escape.

Stay & Play at Our Beautiful Retreat

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat
Chesapeake City Quiet Overlook
Enjoy waterfront dining with a view of the bridge spanning the water.

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (20)
"We attended a wedding across the canal from this house at the Chesapeake Inn. It was very cool to see these really large ships go by as we sat on the deck. Very nice accommodations here! Jane was a great host!"
Chesapeake City Quiet Overlook
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

DoubleTree by Hilton Hotel Wilmington

DoubleTree by Hilton Hotel Wilmington

10/10 Excellent
"We were in the area for a family event, the hotel was close and convenient for us. Enjoyed our stay "
Karen 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Wilmington