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Compare 54 Vacation Homes in Marydel with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (13)
"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.

9.8 out of 10, Exceptional, (18)
"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.

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (10)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

10.0 out of 10, Exceptional, (1)
"We stayed at the property while all our children were at a tournament at the DE turf fields. It was convenient and very comfortable. The house was well supplied and maintained."
Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (76)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Welcome to the waterfront oasis in the serene community of Kitts Hummock Beach!

8.0 out of 10, Very Good, (2)
"This property was perfect for our family. There was plenty of room, the house was very clean, and the location gave us a quiet oasis from the hustle and bustle of the lacrosse tournament. The owner was responsive and fantastic. I think my favorite part was getting to listen to the bay noise at night while going to sleep. Extremely peaceful. Would definitely recommend and hope to stay there again when we are back in the area."
Welcome to the waterfront oasis in the serene community of Kitts Hummock Beach!

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (9)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (80)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Private Yard: Pet-Friendly Home in Dover

10.0 out of 10, Exceptional, (12)
"Quiet location, clean and big. "
Private Yard: Pet-Friendly Home in Dover

Dover Home - 2 Mi to Delaware State University!

9.2 out of 10, Wonderful, (9)
"Clean, quiet and convenient spot for our stay in Dover. "
Dover Home - 2 Mi to Delaware State University!

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

10.0 out of 10, Exceptional, (18)
"Enjoyed all aspects of this property!"
Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Amazing Modern house with a full kitchen and parking

9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
The price is AEDĀ 367
AEDĀ 960 total
includes taxes & fees
12 May - 13 May
Amazing Modern house with a full kitchen and parking

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (68)
"Lovely, well kept and tastefully furnished house in a great location."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Your perfect Maryland escape awaits!

10.0 out of 10, Exceptional, (4)
"Our group had another great stay. The house is exactly as pictured and the host is very responsive. Everything was perfect from checkin to departure. We will definitely stay at this house again!! "
Your perfect Maryland escape awaits!

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

9.8 out of 10, Exceptional, (22)
"We had a great time"
Beautiful, spacious waterfront home, an easy walk to historic Chestertown

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat

10.0 out of 10, Exceptional, (1)
"My stay at Connie's place was like staying in my own house. I had a backyard for my pet and plenty of space if i wanted to entertain. I loved the fact that if you had any questions or problems which i didn't have any problems that Connie was available and if you didn't reach her she got back with you as soon as possible. I would recommend her place if you want a hassle-free vacation that feels like a home and not a hotel. I give her 5 stars on my stay at her bnb. When i do come back to Delaware...
3 Mi to Dover Motor Speedway: Pet-Friendly Retreat

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (5)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!

Quiet Getaway with pool and full of amenity backyard!

Quiet Getaway with pool and full of amenity backyard!
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 Marydel

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

9.8 out of 10, Exceptional, (13)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (84)
"Quiet neighborhood and the best place to stay."
The price is AEDĀ 360
AEDĀ 579 total
includes taxes & fees
13 May - 14 May
First Floor Studio Apartment in Historic Chestertown

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (10)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
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.