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Search Vacation Homes in Middletown

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Compare 129 Vacation Homes in Middletown with updated reviews, rates, and availability.

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "
Chesapeake City Quiet Overlook

New Construction townhome close to everything downtown w/transparent pricing

9.8 out of 10, Exceptional, (11)
"This was a quick trip to Delaware and Lisa’s place was great. Super cute and thoughtful touches throughout. She communicated well with me. Her place is spacious and offers privacy with two separate bedrooms and bathrooms with an additional half bath downstairs. "
The price is SAR 560
SAR 680 total
includes taxes & fees
2 Jan - 3 January 2025
New Construction townhome close to everything downtown w/transparent pricing

Luxurious and spacious townhome with all necessary amenities awaits your stay.

10.0 out of 10, Exceptional, (5)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (7)
"Fabulous townhome a stones throw away from a beautiful river walking path. The house was perfect for our family of 6. The host was fantastic and so quick with responses. The host provided so many extras! If in the area, we would love to stay again. "
The price is SAR 672
SAR 1,299 total
includes taxes & fees
30 Dec - 31 Dec
Private townhouse near downtown and state park

Beautiful Brick-Wall House in Historic Newcastle

7.6 out of 10, Good, (10)
"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

10.0 out of 10, Exceptional, (28)
"This house exceeded our expectations! From the pictures, we knew it would be beautiful, but once we got there it seemed so much bigger and brighter than what the pictures show. Its so light and airy and was perfect for what we came for. It was VERY clean, each bedroom came with towels and makeup wipes. You can tell the hosts put a lot of thought into this home. We went in the fall, but was still such a wonderful time walking along the quiet beach and having drinks on the patio. Would highly...
Beachfront Sunsets on the Water at Oakwood Beach

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.6 out of 10, Exceptional, (43)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

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

9.6 out of 10, Exceptional, (36)
"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Welcome to Woodview Estates!

8.0 out of 10, Very Good, (3)
"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!

Wilmington Comfort 4 Min to Riverfront fenced yard

9.2 out of 10, Wonderful, (18)
"Great value, was a great jumping point for our group, who was here for a wedding"
Wilmington Comfort 4 Min to Riverfront fenced yard

Clean Sanitized upscale suite. One or two beds. Private Bath

9.8 out of 10, Exceptional, (8)
"David did a great job with everything! Everything I needed was available for me"
The price is SAR 315
SAR 537 total
includes taxes & fees
31 Dec - 1 January 2025
Clean Sanitized upscale suite. One or two beds. Private Bath

Right in the center of everywhere in Dover

8.0 out of 10, Very Good, (3)
"Everything was nice enough space for everyone to sleep comfortably."
Right in the center of everywhere in Dover

Upper Chesapeake Getaway - Newly Renovated

9.8 out of 10, Exceptional, (13)
"This home is beautifully decorated, making it most inviting and pleasant. The view of the bay was magical! Sitting on the sun porch was so wonderful! The kitchen was the most well equipped kitchen I’ve had the pleasure to use! Thank you for an amazing stay!!"
Upper Chesapeake Getaway - Newly Renovated

Convenient, spacious 3BR 2.5BA WITH PARKING

10.0 out of 10, Exceptional, (1)
"Very nice townhouse close to lots of stores and restaurants."
Convenient, spacious 3BR 2.5BA WITH PARKING

Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks

10.0 out of 10, Exceptional, (14)
"Perfect house to rent! Clean, spacious, great neighborhood, beautiful property, & very dog friendly! My husband & I rent a different house in different states every year for our anniversary & never go to the same place twice; however, we may have to reconsider as this place was perfect & we may come back! The hot tub & deck(s) were relaxing, the location is great & very quiet, we had fun playing basketball, & we loved the dock and being able to watch the sun rise & set. We suffered the loss of a...
Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks

Your perfect Maryland escape awaits!

10.0 out of 10, Exceptional, (4)
"Property was as described and according to photos. Children’s toys only consisted of card games, and there was no children’s dinnerware which was listed as provided. Kitchen was not well stocked, as there were no baking supplies and we needed to use the oven. Beds were comfortable and there was ample bedding, pillows, blankets, and towels. There was ample parking. Ceiling fans were amazingly quiet and appreciated in each room. Was difficult to use showers only for children’s baths. Property...
Your perfect Maryland escape awaits!

Tip Of The Town Fresh and New 3 Bedroom Nest

9.8 out of 10, Exceptional, (8)
"We had a great stay at this property. Communication was seamless, the property was well taken care of, clean, and well decorated. "
The price is SAR 601
SAR 1,290 total
includes taxes & fees
30 Dec - 31 Dec
Tip Of The Town Fresh and New 3 Bedroom Nest

Charming 3-bedroom house with AC and WiFi in fabulous Newark

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a perfect place for family to stay during our wedding. The house was very clean and very well maintained. Would definitely recommend to anyone. Thanks again for letting us use your home. "
Charming 3-bedroom house with AC and WiFi in fabulous Newark

The Riverside Oasis waterfront with hot tub

10.0 out of 10, Exceptional, (4)
"We arrived to a cozy and warm home decorated beautifully for the holidays. Saturday we went for walks along the water and the kids did some biking. Dinner with our group was enjoyable at the large dining table where everyone had a seat- no need for a kiddy table in this house. Resting our heads down on luxurious bedding and waking up to beautiful water views was a delight. We can’t wait to come back with our clan."
The Riverside Oasis waterfront with 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

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (75)
"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

8.8 out of 10, Excellent, (11)
"Amazing stay. nice quiet clean home. Accommodating for the whole family. Host was easy to connect with very helpful loved our stay ! Looking forward to booking again."
Super cute 3 bedroom remodeled townhouse near downtown Wilmington
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.