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Compare 60 Vacation Homes in Crumpton with updated reviews, rates, and availability.

Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"Beautiful and huge property. Paddling in the river was great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Front of House Facing the Water.
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Room
Amazing Modern house with a full kitchen and parking
Amazing Modern house with a full kitchen and parking
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Exterior
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is SAR 656
SAR 1,018 total
includes taxes & fees
30 Jum. I - 31 Jum. I
BAYSIDE BUNGALOW
Pool table and ping pong able in garage
Dog-Friendly Beach House with Kayaks, Marina & Dive Bar Weekend Access
10.0 out of 10, Exceptional, (10)
"We normally boat on the upper Chesapeake Bay and wanted to boat on different area of the bay. We rented a transient slip at the Tolchester Marina while staying at this bay house. We found the accommodations at this house to be wonderful. The house was clean and well equipped and plenty of space for my family of 7. Probably the most important thing to say - there was an unforeseen issue with the house water system. Jill was extremely concerned and very promptly had technicians coming to the...
Dog-Friendly Beach House with Kayaks, Marina & Dive Bar Weekend Access
From your private pier
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (35)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Large deck off the back of the house with lots of seating, beautiful views.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Relaxation by the Chester River
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
10.0 out of 10, Exceptional, (84)
"This house is a gem! The property is fantastic, with such a beautiful backyard."
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Exterior
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (15)
"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"
Entire Townhouse in Rock Hall
This photo is about 8 years old.  The trees have grown up a little.
Riverfront Country House on The Sassafras River
10.0 out of 10, Exceptional, (12)
"My family had a relaxing, fun weekend at the house. My 20-something children all loved the window seat where they curled up and read. We enjoyed time on the river with the kayaks and paddleboards. The beds were comfy, kitchen well stocked and overall the house is cozy. It was the perfect get-away for our family!"
Riverfront Country House on The Sassafras River
Exterior
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
10.0 out of 10, Exceptional, (2)
"A quick weekend getaway and despite the rain we had a fabulous time! The house was great, location was perfect we just wish we could have spent more time there."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Main Bedroom King - 3rd floor
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
10.0 out of 10, Exceptional, (4)
"My husband and I stayed here for my birthday over President’s Day weekend. The house was absolutely gorgeous and sooo cozy and inviting. It was even better than the pictures and description. While it was only the two of us, there’s plenty of room in the house for a few couples or even two small families. The kitchen is beautiful and modern. The bedroom we stayed in was up on the third floor - king bed - very comfortable and clean. We loved the little balcony off the bedroom (although it was too...
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
The Mellow Yellow Rancher
The Mellow Yellow Rancher near the Chesapeake Bay.
9.8 out of 10, Exceptional, (6)
"The group was me, my 3 sisters and niece. I picked this house because some bedrooms had two beds. We did use the blow up mattress because it was difficult to get in the top bunk bed. I didn’t realize the only coffee pot was a keurig. I brought regular coffee and decaf. Fortunately coffee for the keurig was provided but not decaf. We usually stay closer to the water but this was a good house in our price range."
The Mellow Yellow Rancher near the Chesapeake Bay.
Exterior
In town location with porches and shady patios
9.4 out of 10, Exceptional, (6)
"Loved Rock Hall and comfortable in this home :)"
In town location with porches and shady patios
Welcome to Langford Creek Estate- a beautiful waterfront estate with an extensive amenity list!
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
9.6 out of 10, Exceptional, (4)
"There were some issues with the outdoor area needing to be clean which were immediately rectified. The dock is in disrepair so kayaking wasn’t an option. All in all, a beautiful spacious home."
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Waterfront with private pier and great views
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Property grounds
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (40)
"Beautiful property. Needs better towels and linens. Kitchen is well equipped. Living areas are spacious and comfortable"
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (41)
"This house was beautiful, clean, modern, everything we needed. Loved the huge table and living-room areas where all of us could be together. Weather wasn't great, so we didn't do anything outside, but the house alone was perfect. Host responded quickly, kitchen was fully equipped. Will definitely consider for our next stay!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Betterton Beachhouse - historic Buena Vista,  overlooking the Chesapeake Bay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.4 out of 10, Exceptional, (26)
"This was our second stay here. The property is well appointed for a relaxing stay with 5-star views! Lots of room for family to spread out and relax, and the kitchen has everything you need to make delicious meals. Betterton is extra relaxing with its beautiful views and quiet stillness. We'll be back!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Exterior
Stay in the landmark Lighthouse!
9.8 out of 10, Exceptional, (88)
"Very enjoyable"
Stay in the landmark Lighthouse!
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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.

Other property types in Crumpton

Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"Beautiful and huge property. Paddling in the river was great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Exterior
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is SAR 656
SAR 1,018 total
includes taxes & fees
30 Jum. I - 31 Jum. I
BAYSIDE BUNGALOW
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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