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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 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, (258)
"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

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, (11)
"The unit was perfect for our stay. It was spacious and clean. The location was great, close to restaurants and easy access to major roadways."
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 1,028 total
includes taxes & fees
16 Apr - 17 Apr
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)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
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 2,398 total
includes taxes & fees
15 Apr - 16 Apr
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

10.0 out of 10, Exceptional, (13)
"We had a wonderful get away at a lovely home. It was very clean and decorated nice. We would stay there again. "
The price is AED 551
AED 1,203 total
includes taxes & fees
15 Apr - 16 Apr
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, (12)
"I booked this house for a week as a quiet fishing trip get away. For starters Leone is awesome, always responds quick and is an amazing host.The house itself: was very clean, cozy, and had everything needed for a very comfortable stay. Other reviews said furniture was uncomfortable but I thought it was fine. Location was 3 min to foodlion, 10ish min to gas station, and about 16 min to large store for fishing gear. TV has netflix and lots of other shows to watch if thats what you want but most of...
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..

8.8 out of 10, Excellent, (11)
"Thanks Sean "
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)
"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
15 Apr - 16 Apr
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
22 Apr - 23 Apr
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)
"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
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)
"We travel in the winter in an RV. We had a friend and nephew who we wanted to spend time with and this house was perfect. The weather was very windy but having the beach right out the door was.perfect motovation to "
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)
"Beautiful large home .Room for everyone.Kitchen is wonderful.Location is perfect .Will most diffently rent again .Kim is a fantastic host ."
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)
"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!
White Clay Creek Cottage
Terrace/patio

White Clay Creek Cottage

10.0 out of 10, Exceptional, (3)
"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. "
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)
"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
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!
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

The price is AED 496
AED 1,028 total
includes taxes & fees
16 Apr - 17 Apr
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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)
"We travel in the winter in an RV. We had a friend and nephew who we wanted to spend time with and this house was perfect. The weather was very windy but having the beach right out the door was.perfect motovation to "
Beachfront Sunsets on the Water at Oakwood Beach
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
Private kitchen

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

"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 AED 404
AED 683 total
includes taxes & fees
15 Apr - 16 Apr
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
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.