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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
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Relax in a serene backyard oasis with Adirondack chairs, a table, and a chair, surrounded by a fence.

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

9.6 out of 10, Exceptional, (59)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Cozy Farmhouse in Greenville, DE
Enjoy cooking in this well-equipped kitchen with ample counter space and a large island.

Cozy Farmhouse in Greenville, DE

10.0 out of 10, Exceptional, (24)
"Super clean house that’s perfect for a group gathering "
Cozy Farmhouse in Greenville, DE
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
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a granite countertop.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (19)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
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
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!
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
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Enjoy a serene sea view from this inviting space with a wooden ceiling, glass door to a deck, and a cozy seating area.

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

9.2 out of 10, Wonderful, (179)
"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
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Enjoy serene waterfront views and easy access to boating.

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
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
Sailor's Sunrise Cottage - Chesapeake Bay
Outdoor spa tub

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (49)
"Landscaping was a little lacking. We're older so the low furnishings were a little challenging, but overall; very relaxing and pretty much what we expected. "
Sailor's Sunrise Cottage - Chesapeake Bay
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 $413 total
includes taxes & fees
Aug 18 - Aug 19
Private townhouse near downtown and state park
5-bedroom vacation home 5 minutes from historic Charlestown
Enjoy a serene lakeside retreat with a grassy area, sandy beach, and dock for boating and fishing.

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is CA $462
CA $857 total
includes taxes & fees
Aug 11 - Aug 12
5-bedroom vacation home 5 minutes from historic Charlestown
Captivating Chesapeake experience
Relax on the pier with a view of distant landforms.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (270)
"Beautiful home and setting!"
Captivating Chesapeake experience
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!
Welcome to Woodview Estates!
Staircase leads to an upper level in this stylish room with a side table and lamp.

Welcome to Woodview Estates!

7.6 out of 10, Good, (4)
"The house was perfect for our stay. We were in town for a family event and needed a place for 8 adults and 4 children and this was perfect. Lots of space to spread out with a great rec room that kept both kids and adults entertained during down time. The neighborhood was beautiful and had easy access to area restaurants and shopping. Close to many area attractions. It was the perfect location to have close proximity to points of interest and then return to at end of day to a relaxing...
Welcome to Woodview Estates!
Clean and Cozy 2 BR home blocks away from downtown
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a microwave, oven, and dishwasher, set against a sleek black granite countertop.

Clean and Cozy 2 BR home blocks away from downtown

10.0 out of 10, Exceptional, (28)
"Very easy to walk to the downtown area and such a lovely property. Will stay here again if we come back to the North East area"
Clean and Cozy 2 BR home blocks away from downtown
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
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

Holiday Inn Express And Suites Middletown by IHG

Holiday Inn Express And Suites Middletown by IHG

10/10 Excellent
"Nice"
Jacob 1-night trip
Posted 1 day ago
Holiday Inn Express And Suites Middletown by IHG