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Search results; Over 1,000 homes in Trappe

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Resort in Trappe
The Mayflower
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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5.0 out of 5 average rating, 39 reviews
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Guest favourite
Resort in Trappe
Sequoia Suite
2 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 32 reviews
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Home in Cambridge
Walk to Eagleman & Ironman Historic Cambridge Stay
6 bedrooms, 6 beds
2–7 Jan
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Top guest favourite
Home in Chester
Waterfront home w/ HotTub, Dock, FirePit, GameRoom
4 bedrooms, 4 king beds
19–24 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Townhouse in Selbyville
‘Dockside Retreat’ -pool, minutes to OC/beaches
3 bedrooms, 5 beds
11–16 Oct
5.0 out of 5 average rating, 67 reviews
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Superhost
Home in Royal Oak
Waterfront, Hot Tub, Elevator. Waterfowl Special!
4 bedrooms, 6 beds
25–30 Sept
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Top guest favourite
Flat in Cambridge
Happy Campers Waterfront Suite
1 bedroom, 1 queen bed
5–10 Oct
4.97 out of 5 average rating, 74 reviews
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Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 253 reviews
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Top guest favourite
Cottage in Piney Point
Beach Access | Waterfront Views | Kayaks & Bikes
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 50 reviews
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Home in Colonial Beach
Beach House Retreat on the Docks.
3 bedrooms, 3 beds
23–28 Sept
New place to stay
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Guest favourite
Home in Hebron
The Whole Fam-damily
4 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Stevensville
Bay Bliss House
3 bedrooms, 3 beds
23–28 Sept
5.0 out of 5 average rating, 42 reviews
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Home in Piney Point
Beachfront Home - 10
2 bedrooms, 6 beds
28 Sept – 3 Oct
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Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
2 bedrooms, 3 beds
13–18 Oct
5.0 out of 5 average rating, 125 reviews
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Top guest favourite
Home in Lusby
Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
4 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 46 reviews
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Top guest favourite
Cabin in Hague
Rustic Waterfront Cabin, Firepit, Dock Access
3 bedrooms, 5 beds
21–26 Sept
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 146 reviews
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Home in Preston
The Hatting Homestead
3 bedrooms, 7 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds
22–27 Sept
5.0 out of 5 average rating, 5 reviews