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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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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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Room in Deale
Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual
1 bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 13 reviews
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Flat in Pasadena
Relaxing Waterfront Apartment!
3 bedrooms, 4 beds, 1.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 55 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, 7 reviews
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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
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Cabin in Accident
Rustic Luxe Cabin (4x4 Required)
2 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 99 reviews
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Cottage in North East
Vintage Waterfront Cottage with Stunning Sunsets
2 bedrooms, 4 beds, 2.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 66 reviews
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Home in Solomons
The Little House on Back Creek
2 bedrooms, 2 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 143 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 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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Guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 15 reviews
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Home in Hollywood
Waterfront Home: Osprey Getaway
4 bedrooms, 6 beds, 3 bathrooms
1–6 Oct
4.99 out of 5 average rating, 109 reviews
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Cabin in Frederick
Misty Hill Lodge-Frederick
2 bedrooms, 2 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 133 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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Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 100 reviews
Photo 1 of 29
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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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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, 125 reviews