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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 92 Vacation Homes in Crumpton with updated reviews, rates, and availability.

BAYSIDE BUNGALOW
Exterior detail

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 1,098 total
includes taxes & fees
1 Jun - 2 Jun
BAYSIDE BUNGALOW
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, (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
Fridge, microwave, oven, stovetop

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
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, (38)
"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.
Interior

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

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!
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, (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
Fridge, microwave, oven, stovetop

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
Dining

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
Beach towels

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

9.8 out of 10, Exceptional, (60)
"Great place near the marina. Kitchen was well equipped for cooking our own meals. Nice recent updates to the bathroom and kitchen. Covered porch out back is also quite nice. We enjoyed our stay and would gladly return to this house!"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Waterfront family resort Lodge with private pier, game room and bar
Game room

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

9.8 out of 10, Exceptional, (25)
"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!
Beach

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

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

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
Welcome to Mermaid Haven! The perfect spacious home for your Rock Hall vacaction
Beach nearby, sun loungers, beach towels

Welcome to Mermaid Haven! The perfect spacious home for your Rock Hall vacaction

9.4 out of 10, Exceptional, (13)
"This was our second stay at this location and, as with our first stay, everything was perfect."
Welcome to Mermaid Haven! The perfect spacious home for your Rock Hall vacaction
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Fridge, microwave, oven, stovetop

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.6 out of 10, Exceptional, (7)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Marina

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

10.0 out of 10, Exceptional, (14)
"Extremely clean, comfortable, and cozy place to stay for a weekend trip. The host was great to work with. We would definitely stay again."
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Waterfront! Sunroom, Private Dock, Boat Tie-Up & Near Town
Fridge, microwave, oven, stovetop

Waterfront! Sunroom, Private Dock, Boat Tie-Up & Near Town

Waterfront! Sunroom, Private Dock, Boat Tie-Up & Near Town
Spacious 4-bedroom house with AC and WiFi in charming Kennedyville
Fridge, microwave, oven, stovetop

Spacious 4-bedroom house with AC and WiFi in charming Kennedyville

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was well maintained and convenient to the college"
Spacious 4-bedroom house with AC and WiFi in charming Kennedyville
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (26)
"The house is comfortable, clean and the location is fantastic. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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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