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Compare 87 Vacation Homes in Crumpton with updated reviews, rates, and availability.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (53)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

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.

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

9.8 out of 10, Exceptional, (13)
"Beautiful house, perfect for our family. The humans loved kayaking and bird watching on the river, the canine loved sitting out on the fenced in deck and relaxing in the nice cool AC"
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, (16)
"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

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite

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

10.0 out of 10, Exceptional, (25)
"The house is comfortable, clean and the location is fantastic. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

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

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!

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"A very nice and clean property to stay and rest. My daughter and I had a great time walking around Rock Hall and visiting the beach! A very nice neighborhood near downtown Rock Hall to go and see items of interest in the town but be able to go back to the property to rest and cook our meals. An excellent stay and visit!"
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

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

9.4 out of 10, Exceptional, (33)
"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!

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

10.0 out of 10, Exceptional, (2)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 643
AED 997 total
includes taxes & fees
4 May - 5 May
BAYSIDE BUNGALOW

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (98)
"We stayed at the light house for three nights in celebration of the new year, 2025. It was a work vacation involving winter covering of our sailboats as well as celebrating the new year. We thoroughly enjoyed our time together and will come here again."
Stay in the landmark Lighthouse!

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (27)
"This duplex was as listed, clean, walkable to the stores & waterfront restaurants, would recommend for a quiet getaway."
Entire Townhouse in Rock Hall

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

10.0 out of 10, Exceptional, (13)
"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!

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

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

10.0 out of 10, Exceptional, (17)
"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 AED 367
AED 960 total
includes taxes & fees
7 May - 8 May
Amazing Modern house with a full kitchen and parking

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
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 Crumpton

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 643
AED 997 total
includes taxes & fees
4 May - 5 May
BAYSIDE BUNGALOW

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (47)
"We really enjoyed the water views & walking by the water. It was a very enjoyable and relaxing stay."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
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.