Search Vacation Homes in Sudlersville

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

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (38)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is AED 735
AED 1,102 total
includes taxes & fees
3 Jun - 4 Jun
BAYSIDE BUNGALOW

3 Mi to Dtwn: Townhome w/ Deck in Dover

3 Mi to Dtwn: Townhome w/ Deck in Dover

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

9.6 out of 10, Exceptional, (14)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

10.0 out of 10, Exceptional, (12)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

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

9.6 out of 10, Exceptional, (39)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (47)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (15)
"Perfect for a family wedding weekend"
River Front, Private Single Family Home

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!

10.0 out of 10, Exceptional, (20)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!

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

10.0 out of 10, Exceptional, (22)
"Stayed for 2 nights while we were hunted nearby "
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (1)
"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

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

10.0 out of 10, Exceptional, (77)
"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!

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (68)
"Enjoyed the stay and house very comfortable."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

9.8 out of 10, Exceptional, (60)
"It’s a nice place"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (6)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"We had a great stay. The house was very comfortable and had everything one could need. Clean linens. Done up with a great aesthetic sensibility. The view was fantastic. Everything was just perfect!"
Grasonville Home w/ Private Pool on the Water

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (26)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (98)
"Thanks for a great stay! The house was perfect and so well stocked! Can't wait to stay there again!"
Stay in the landmark Lighthouse!

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (62)
"Bigger, nicer and newer than it looks in the pics; a pleasant surprise. Great location, we’d go again. "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

9.6 out of 10, Exceptional, (34)
"This was the best Christmas yet and on top of that, the home was amazing, great amenities, great view, great time. Thank you to the host! "
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + 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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