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Compare 127 Vacation Homes in Middletown with updated reviews, rates, and availability.

2 Master Bedrooms each w/private full baths. Quick drive or walk to everything!
9.8 out of 10, Exceptional, (7)
"My friend and I were meeting between DC and NY and this was the perfect spot! We each had our own bedroom and bathroom and there was another bathroom downstairs so we didn’t have to run upstairs. Comfortably furnished and everything you need if you are staying in, conveniently located to Philly and other cute little towns in the surrounding area. Neighborhood was busy on Saturday night but we felt safe and enjoyed our stay! The boat was great with suggestions and responsive to our needs. She...
The price is SAR 732
SAR 874 total
includes taxes & fees
23 Sep - 24 Sep
2 Master Bedrooms each w/private full baths. Quick drive or walk to everything!
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (51)
"Location is great and Suzanne is quick to respond and willing to help. We had a good time."
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (249)
"We had a wonderful stay at this beautiful property. The water views are amazing and it was so relaxing! The house was very clean and well maintained. Everything we expected it to be from the listing, actually more charming and comfortable than the pictures show. Thank you. "
Captivating Chesapeake experience
Ultimate Retreat @ Papermill Rd
10.0 out of 10, Exceptional, (4)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd
Home Away from Home - Local Shops, Restaurants & Grocery stores within 4 miles!
9.4 out of 10, Exceptional, (3)
"Great place, Great host ! Will definitely stay here again. Highly recommended."
The price is SAR 732
SAR 1,269 total
includes taxes & fees
23 Sep - 24 Sep
Home Away from Home - Local Shops, Restaurants & Grocery stores within 4 miles!
Luxurious and spacious townhome with all necessary amenities awaits your stay.
10.0 out of 10, Exceptional, (1)
"Great place!!! We enjoyed our stay and amenities. Well worth the price. Shopping and family fun!!!"
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (93)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
Waterfront house with amazing views. Top of the Chesapeake
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, (33)
"Debbie was a great communicator and very generous with allowing us to check in early - such a treat! The kitchen is well appointed and we were all impressed with the great bath towels and bed linens. The one thing to point out is that while this is a water front property, I didn't realize from the pictures, that its on a cliff, so you couldn't fish from the front of the property like I was imagining prior to arriving; luckily the walk to the beach was a short one so our kiddos fished from...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, (133)
""Oh, down in Chesapeake Catching rock around fishing creek The soft-shell crabs play hide and seek Down in Chesapeake." We LOVE the Chesapeake area and have stayed up and down the bay, mostly midway and lower. This area on the upper bay is so close to Philadelphia and, although there are tourists around like us, it doesn't feel touristy unless you go into North East, downtown (which is still worth eating a meal or getting ice cream in that cute little town)! Our stay felt private, and we had...
The price is SAR 1,235
SAR 2,299 total
includes taxes & fees
23 Sep - 24 Sep
Top of the Chesapeake - Minutes from Historic Charlestown
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
Historic home in the heart of Main Street- walkable to shops and restaurants
Sweet Little Home Away From Home, North East, MD
Sweet Little Home Away From Home, North East, MD
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (23)
"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
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, (39)
"Perfect place to get away and relax by the bay. Awesome waterfront access made paddle boarding a breeze! Everything was beautiful and the outside amenities made enjoying the view even better."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
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
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (95)
"Older home that was very clean. met our needs well. was close to the University of Delaware. "
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Hidden Gem! - Downtown
7.4 out of 10, Good, (3)
"This is my second time staying, the host always make me feel comfortable. This will be my go to everytime I visit this area."
Hidden Gem! - Downtown
Wilmington Comfort 4 Min to Riverfront fenced yard
9.2 out of 10, Wonderful, (17)
"Great"
Wilmington Comfort 4 Min to Riverfront fenced yard
Clean and Cozy 2 BR home blocks away from downtown
10.0 out of 10, Exceptional, (18)
"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
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
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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

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (27)
"The accomodations were VERY nice. The wifi was not sufficient for me to work in the room, but they allowed us to sit on the deck and work instead."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (51)
"Location is great and Suzanne is quick to respond and willing to help. We had a good time."
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (23)
"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
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.