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Search results; Over 1,000 places

Guest favourite
Home in Rock Hall
Chesapeake Bay Retreat w/ Views!
4 beds
12–17 May
5.0 out of 5 average rating, 16 reviews
Guest favourite
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
1 double bed
21–26 Apr
4.98 out of 5 average rating, 292 reviews
Superhost
Home in Irvington
Retreat to Wooded Fairytale Cottage with Pool
3 beds
22–27 Apr
New place to stay
Guest favourite
Tiny home in Solomons
“Cabana by the Bay”-tiny home on a pier!
1 double bed
4–9 Aug
4.95 out of 5 average rating, 536 reviews
Guest favourite
Home in Heathsville
Water ft Chesapeake Bay DREaM Vacation Dock Kayaks
3 beds
22–27 Apr
4.93 out of 5 average rating, 122 reviews
Home in Scotland
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
5 beds
5–10 May
5.0 out of 5 average rating, 10 reviews
Guest favourite
Cabin in Reedville
Dinna Fash-3 BR Waterfront Log Cabin
3 beds
21–26 Apr
4.97 out of 5 average rating, 188 reviews
Guest favourite
Treehouse in Machipongo
Treehouse Couple's Retreat
On Smith BeachKayak, Boat ramp,
30 Jul – 4 Aug
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
2 beds
7–12 Jul
4.96 out of 5 average rating, 24 reviews
Superhost
Cottage in Reedville
Bay cottage 🏖on the beach. Stunning views🏝
5 beds
21–26 Apr
4.88 out of 5 average rating, 153 reviews
Guest favourite
Place to stay in Airville
~NEW~Waterfront Log Cabin with Hot Tub
1 queen bed
7–12 Dec
4.94 out of 5 average rating, 69 reviews
Guest favourite
Cottage in Urbanna
Little Dipper -private beach,Kayaks & paddleboards
3 beds
6–11 May
4.99 out of 5 average rating, 134 reviews
Guest favourite
Home in Ridge
Vacation Rental House Situated on Chesapeake Bay
6 beds
21–26 Apr
5.0 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Westover
Rumbley Cottage on the Tangier Sound-Private Beach
2 queen beds
29 Oct – 3 Nov
4.99 out of 5 average rating, 180 reviews
Guest favourite
Home in North
The Llama House
1 bed
7–12 May
5.0 out of 5 average rating, 36 reviews
Guest favourite
Tiny home in Machipongo
Machipongo Glamper
1 double bed
2–7 Jun
4.98 out of 5 average rating, 253 reviews
Guest favourite
Tiny home in Cape Charles
The Laughing King Retreat Honeymoon Island Cottage
1 king bed
28 Apr – 3 May
4.98 out of 5 average rating, 271 reviews
Guest favourite
Cabin in Cape Charles
Ultimate Cabin Farm Stay Cape Charles
On the lakeLake views,
24–29 Jun
4.97 out of 5 average rating, 96 reviews