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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
1–6 Oct
4.99 out of 5 average rating, 343 reviews
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Top guest favourite
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, 8 reviews
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Flat in Cambridge
Lairds Cove
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
New place to stay
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Top guest favourite
Home in North Beach
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 189 reviews
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Top guest favourite
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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Top guest favourite
Home in Hollywood
Waterfront Home: Osprey Getaway
4 bedrooms, 6 beds, 3 bathrooms
2–7 Oct
4.99 out of 5 average rating, 109 reviews
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Home in Cambridge
Sandy Point: a waterfront home on the cove
3 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
New place to stay
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Top guest favourite
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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Home in Frederick
Grace on Trail
3 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 100 reviews
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Home in Manchester
Peaceful Farm House / Large Yard / Privacy / Quiet
4 bedrooms, 6 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Farm stay in Damascus
Large countryside escape
3 bedrooms, 6 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 127 reviews
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Top guest favourite
Cottage in Tall Timbers
Charming Waterfront Cottage with Sunset Views
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 80 reviews
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Top guest favourite
Home in Cambridge
Chesapeake Bay Retreat
6 bedrooms, 14 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Farm stay in Lothian
The Old Tucker Farm
4 bedrooms, 5 beds, 3 bathrooms
10–15 Nov
New place to stay
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Top guest favourite
Home in Lusby
Historic Rousby Hall, Waterfront, Pool, Beach
4 bedrooms, 4 beds, 4 bathrooms
12–17 Nov
4.99 out of 5 average rating, 179 reviews
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Guest favourite
Farm stay in Woodsboro
Farm Retreat- Sauna, Hot Tub, Cold Plunge, Trails
4 bedrooms, 4 beds, 2 bathrooms
13–18 Dec
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 175 reviews