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Vacation Homes in Marydel

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

9.8 out of 10, Exceptional, (12)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (72)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

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

9.8 out of 10, Exceptional, (81)
"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

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

10.0 out of 10, Exceptional, (56)
"We had a fantastic time- the location on the water was gorgeous and loved the hot tub and pool. Extremely quiet and private!"
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

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

10.0 out of 10, Exceptional, (14)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Turnbridge Manor

9.8 out of 10, Exceptional, (11)
"We rented this wonderful home for Christmas and had the most relaxing time. The house is just as advertised and the owner a delight to work with. We especially loved the proximity to the square and how walkable it was to everything. I can’t wait to rent it again during warm weather to enjoy all the wonderful porches and the outdoor area."
$575 nightly
The price is $610
Jul 15 - Jul 16
Total includes taxes and fees
Turnbridge Manor

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

10.0 out of 10, Exceptional, (3)
"Great location for sports tournaments at the DE turf fields! House was super clean, cool, comfortable and little things like chairs were an added bonus! And host was very responsive!"
Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (11)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!

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

10.0 out of 10, Exceptional, (81)
"Loved our stay!"
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (7)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Spacious 5 Bedroom w/Pool, Patio and Theater

9.6 out of 10, Exceptional, (5)
"Great house for a large family "
Spacious 5 Bedroom w/Pool, Patio and Theater

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!

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

9.6 out of 10, Exceptional, (17)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Countryside Cottage in Sassafras

2.0 star property
Countryside Cottage in Sassafras

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room

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. "
$302 nightly
The price is $308
Jul 27 - Jul 28
Total includes taxes and fees
Amazing Modern house with a full kitchen and parking

3 Mi to Dtwn: Townhome w/ Deck in Dover

10.0 out of 10, Exceptional, (2)
"Absolutely beautiful home! Our stay was very comfortable and relaxing. The host was extremely gracious."
3 Mi to Dtwn: Townhome w/ Deck in Dover

Adorable two-bedroom retreat close to Easton, Denton, Centreville

10.0 out of 10, Exceptional, (24)
"Stayed for 2 nights while we were hunted nearby "
Adorable two-bedroom retreat close to Easton, Denton, Centreville

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!

Dover Home - 2 Mi to Delaware State University!

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