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Vacation Homes in Crumpton

Our top choices for Crumpton vacation homes

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

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.

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

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

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 SAR 751
SAR 1,122 total
includes taxes & fees
8 Sep - 9 Sep
BAYSIDE BUNGALOW

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

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.

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!

10.0 out of 10, Exceptional, (24)
"Everything about this rental was perfect! "
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

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!

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

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

10.0 out of 10, Exceptional, (1)
"Beautiful home. Gorgeous views of Bohemian River. Well maintained House and fully supplied. Our families and friends just loved it. They were already speaking about wanting to return again. "
Waterfront Lodge packed with Amenities

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

9.8 out of 10, Exceptional, (84)
"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

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

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is SAR 740
SAR 1,683 total
includes taxes & fees
16 Sep - 17 Sep
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (14)
"A large sprawling house that’s perfect for groups, this property offers stunning views of the Chester River. We spent every evening of our stay sitting along the water. "
Pet-Friendly Home on Chester River w/ Dock!

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2.0 star property
8.6 out of 10, Excellent, (4)
"Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests."
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

200 steps to the beach!

10.0 out of 10, Exceptional, (90)
"Great stay - it met all of our needs."
200 steps to the beach!

Waterfront in Historic Rock Hall, overlooking the main harbor and Chesapeake Bay

9.8 out of 10, Exceptional, (10)
"Property was extremely well kempt. It was beautiful. We enjoyed ourselves there and would recommend it to others."
Waterfront in Historic Rock Hall, overlooking the main harbor and Chesapeake Bay
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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Top Crumpton Hotel Reviews