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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 132 Vacation Homes in Middletown with updated reviews, rates, and availability.

Beachfront Sunsets on the Water at Oakwood Beach
On the beach, sun loungers, beach towels

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (32)
"Our family had a wonderful weekend all under one roof…every parents dream once your children become adults. The house was perfect for us…6 adults, our 2 year old granddaughter and a little dog. The house was clean, comfortable and had an amazing view of the water. We were lucky enough to witness 2 incredible sunsets! Our host, John, was very accommodating and easy to chat with. Throughly enjoyed our stay at this wonderful house. "
Beachfront Sunsets on the Water at Oakwood Beach
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
Living area

Cozy on the Hill. Close to Riverfront, Brandywine park and great food

9.8 out of 10, Exceptional, (9)
"It was fine"
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

The price is AED 496
AED 1,016 total
includes taxes & fees
10 Mar - 11 Mar
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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, (11)
"Clean, cute little house, convenient location"
The price is AED 569
AED 1,222 total
includes taxes & fees
10 Mar - 11 Mar
Tip Of The Town Fresh and New 3 Bedroom Nest
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (11)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Beach

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (16)
"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"
The price is AED 2,071
AED 4,064 total
includes taxes & fees
10 Mar - 11 Mar
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Newly renovated single family home with attached guest suite
Smart TV

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite
Beautiful Brick-Wall House in Historic Newcastle
Fridge, microwave, oven, stovetop

Beautiful Brick-Wall House in Historic Newcastle

8.0 out of 10, Very Good, (11)
"The location was ideal considering it was located at a reasonable distances to all places I had to go to. Short or moderate drive to about 5 different locations."
Beautiful Brick-Wall House in Historic Newcastle
Clean and Cozy 2 BR home blocks away from downtown
Fridge, microwave, oven, stovetop

Clean and Cozy 2 BR home blocks away from downtown

10.0 out of 10, Exceptional, (20)
"Phyllis’ home was 100% newly remodeled and impeccably clean! We enjoyed a wonderful stay in her comfortable home. The fresh flowers were a welcome surprise after a long drive, and Phyllis checked in on us via text to make sure we made it there safely. Recommend! "
Clean and Cozy 2 BR home blocks away from downtown
Guest Lodge | Private Pool | Outdoor Dining | Game Room
Exterior

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (35)
"Our family stayed here for 5 nights. The house was updated and beautiful! It was stocked with all of our basic needs and the owners quickly responded to any questions, as well as provided suggestions for local places to check out. We especially enjoyed hiking area trails, including the lighthouse, and walking and shopping in North East. It was an enjoyable and relaxing stay. Thank you for your hospitality!"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
3 Mi to Dover Motor Speedway: Pet-Friendly Retreat
Fridge, microwave, stovetop, dishwasher

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Dining

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

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Fridge, microwave, oven, stovetop

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

8.6 out of 10, Excellent, (10)
"The house had plenty of space and location was great!"
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Exterior

House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.

9.8 out of 10, Exceptional, (102)
"House was great yet again. Betsy always has the place clean and ready for us!!"
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Wilmington Comfort 4 Min to Riverfront fenced yard
Fridge, microwave, oven, stovetop

Wilmington Comfort 4 Min to Riverfront fenced yard

9.2 out of 10, Wonderful, (20)
"Host was helpful with great communication. Property was clean, spaceous and pet friendly. Great experience over all. Only negative feedback to provide is the neighborhood did not feel safe. "
Wilmington Comfort 4 Min to Riverfront fenced yard
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (136)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is AED 1,319
AED 2,398 total
includes taxes & fees
10 Mar - 11 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
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, (55)
"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

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

9.4 out of 10, Exceptional, (169)
"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
Saybrook Hall | Pickleball + Pool + Hot Tub
Pool

Saybrook Hall | Pickleball + Pool + Hot Tub

Saybrook Hall | Pickleball + Pool + Hot Tub
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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Other property types in Middletown

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

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

9.4 out of 10, Exceptional, (22)
"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.
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Fridge, microwave, oven, stovetop

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

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
Living area

Cozy on the Hill. Close to Riverfront, Brandywine park and great food

9.8 out of 10, Exceptional, (9)
"It was fine"
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
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.