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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"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
River Front, Private Single Family Home
Property grounds

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (19)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home
Entire Townhouse in Rock Hall
Exterior

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "
Entire Townhouse in Rock Hall
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Dining

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"The property is everything it claims to be & more. Awesome location on the bay. Great accommodations. So peaceful. We had a wonderful time. Would highly recommend! "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Peaceful Queenstown Home w/ Deck & Grill!
Interior

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Enjoyed this lovely and comfortable home tucked away in a private location close to amenities. "
Peaceful Queenstown Home w/ Deck & Grill!
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (47)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is HK$1,559
HK$2,363 total
includes taxes & fees
2 Sept - 3 Sept
BAYSIDE BUNGALOW
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Property grounds

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"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
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (21)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Property grounds

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

10.0 out of 10, Exceptional, (23)
"Everything about this rental was perfect! "
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Grasonville Home w/ Private Pool on the Water
Pool

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (23)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is HK$1,949
HK$3,214 total
includes taxes & fees
2 Sept - 3 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Waterfront Estate w Private Pier, Game Room & Bar
Games room

Waterfront Estate w Private Pier, Game Room & Bar

9.8 out of 10, Exceptional, (31)
"We take a family vacation every year and this was so perfect! Great for the kids. "
Waterfront Estate w Private Pier, Game Room & Bar
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

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!
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Beach nearby

Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD

10.0 out of 10, Exceptional, (20)
"We really enjoyed our stay in Rock Hall! Perfect house in a great location."
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Waterfront Lodge packed with Amenities
Pool

Waterfront Lodge packed with Amenities

Waterfront Lodge packed with Amenities
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Property grounds

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

10.0 out of 10, Exceptional, (11)
"We loved our stay! "
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Terrace/patio

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

9.8 out of 10, Exceptional, (83)
"Loved the location next to the river. Spent a lot of time on the dock and in the yard. Proximity to Chestertown a real plus too. Great hosts!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
WATERFRONT right on a BEACH
On the beach, beach towels

WATERFRONT right on a BEACH

10.0 out of 10, Exceptional, (51)
"Great property very quit and relaxing"
WATERFRONT right on a 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.
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