Photo by Michelle Gonzalez

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 187 Vacation Homes in Middletown with updated reviews, rates, and availability.

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Fridge, microwave, oven, stovetop

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

The price is AED 511
AED 607 total
includes taxes & fees
27 May - 28 May
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, (12)
"Perfect place to stay for an extended work trip. The host is responsive, accommodating and was great to work with. "
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

9.0 out of 10, Wonderful, (2)
"Nice and quiet place to stay"
The price is AED 496
AED 1,032 total
includes taxes & fees
6 May - 7 May
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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, (37)
"This 3 bedroom, 2 bath Cottage was perfect! Our family enjoyed staying there. We found the home to be clean, well equipped and comfortable."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
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 2,379 total
includes taxes & fees
8 May - 9 May
5-bedroom vacation home 5 minutes from historic Charlestown
Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

9.4 out of 10, Exceptional, (16)
"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
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, (13)
"Beautiful house, perfect for our family. The humans loved kayaking and bird watching on the river, the canine loved sitting out on the fenced in deck and relaxing in the nice cool AC"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
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..

8.2 out of 10, Very Good, (12)
"The house had plenty of space and location was great!"
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
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)
"The home was perfect for our family of 10. We spent most of our time on the beautiful screened in porch overlooking the river. The location was within a 5 min drive to all our favorite restaurants. The owners are very accommodating and quick to answer any questions. "
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Cozy 2-bedroom townhome in charming Elkton
Fridge, microwave, oven, stovetop

Cozy 2-bedroom townhome in charming Elkton

8.0 out of 10, Very Good, (1)
"The house itself was clean. Had everything we needed. It seemed like the back yard was still being cleared of trees and debris. Was too chilly for sitting out though. All and all, was fine."
The price is AED 422
AED 526 total
includes taxes & fees
4 May - 5 May
Cozy 2-bedroom townhome in charming Elkton
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)
"convenient to northern Delaware and southeastern PA attractions"
Beautiful Brick-Wall House in Historic Newcastle
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, (33)
"The house was great for a girls weekend and the host was very communicative and helpful with finding places to eat/drink as we weren’t familiar with the area. "
Beachfront Sunsets on the Water at Oakwood Beach
Cozy Farmhouse in Greenville, DE
Fridge, microwave, oven, stovetop

Cozy Farmhouse in Greenville, DE

10.0 out of 10, Exceptional, (17)
"Super clean house that’s perfect for a group gathering "
Cozy Farmhouse in Greenville, DE
Nancy’s Touch, A Waterfront Paradise!
Property grounds

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (159)
"This was a great Property, with a Great View. Wife & her sister, and 98yr old Mother really enjoyed it."
Nancy’s Touch, A Waterfront Paradise!
White Clay Creek Cottage
Terrace/patio

White Clay Creek Cottage

10.0 out of 10, Exceptional, (4)
"Perfect cottage stay and convenient proximity to Newark DE, Christiana, Longwood Gardens, PA. The owners are very accommodating. Extremely comfortable beds, sofas, and nicely appointed. "
The price is AED 364
AED 724 total
includes taxes & fees
5 May - 6 May
White Clay Creek Cottage
Short Term & Long Term Rental Dogs Allowed Upon Approval
Fridge, microwave, oven, stovetop

Short Term & Long Term Rental Dogs Allowed Upon Approval

9.6 out of 10, Exceptional, (20)
"This home was GORGEOUS with every amenity and close to everything. The host was the best. Wrote back right away. Sent someone to help shovel the driveway when it snowed. Could not have been nicer and more accommodating. Absolutely perfect."
Short Term & Long Term Rental Dogs Allowed Upon Approval
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)
"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
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)
"Host was excellent making sure we had everything we needed and more for a comfortable stay. The home was very cozy and comfortable like being in your own home. We will definitely be returning! "
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
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

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

9.0 out of 10, Wonderful, (2)
"Nice and quiet place to stay"
The price is AED 496
AED 1,032 total
includes taxes & fees
6 May - 7 May
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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.

9.6 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.
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
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.