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Photo 1 of 29
Top guest favourite
Treehouse in Swanton
The Overlook; A Romantic Treehouse for Two
1 bedroom, 1 bed, 1 bathroom
30 Nov – 5 Dec
4.99 out of 5 average rating, 343 reviews
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Cottage in North Beach
Waterfront Cottage Near Herrington and North Beach
2 bedrooms, 3 beds, 2 bathrooms
10–15 Nov
4.97 out of 5 average rating, 381 reviews
Photo 1 of 24
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Home in Frederick
Firepit Patio Retreat · Downtown Frederick 2BR
2 bedrooms, 2 queen beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
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Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
2 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 125 reviews
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Home in Woodlawn
Private 1BR & Living Room W/Private Entrance
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 26
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Home in Greensboro
Cozy 2 bedroom home on wooded private lane
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Sept
4.97 out of 5 average rating, 145 reviews
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Guest suite in Grasonville
Heron's Haven
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 141 reviews
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Cabin in Frederick
Misty Hill Lodge-Frederick
2 bedrooms, 2 beds, 2 bathrooms
7–12 Oct
4.98 out of 5 average rating, 132 reviews
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Home in Sharpsburg
Steps to Winery and Battlefield – 1 Acre Retreat
3 bedrooms, 3 queen beds, 1 bathroom
4–9 Nov
4.96 out of 5 average rating, 248 reviews
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Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 314 reviews
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Home in Stevensville
Private & Peaceful Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 6 reviews
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Home in Stevensville
Kent Island Waterfront | Swim Spa + Sauna + Beach
4 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 28 reviews
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Home in Lusby
Sandy Beachfront A-Frame w/ Hottub & Private Dock
4 bedrooms, 7 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 23 reviews
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Guest house in Cambridge
The Loft at Sailor's Retreat. Waterfront Apartment
1 bedroom, 1 king bed, 1 bathroom
29 Oct – 3 Nov
4.99 out of 5 average rating, 122 reviews
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Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 175 reviews
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Tiny home in Aberdeen
Private Tiny Home near Havre de Grace attractions
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 23 reviews
Photo 1 of 29
Guest favourite
Home in Frederick
Sugarloaf Mountain Retreat- 300 Acre Estate
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 78 reviews
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Home in Columbia
Lakefront Couples Escape | Fire Pit |Sunset Views
1 bedroom, 1 king bed, 1 bathroom
5–10 Oct
4.98 out of 5 average rating, 45 reviews