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Search results; Over 1,000 places
Over 1,000 places
Guest favorite
Guest favorite
Treehouse in Swanton
The Overlook
Apr 24 – 29
Apr 24 – 29
$242
night
$242 per night
4.98 out of 5 average rating, 59 reviews
4.98 (59)
Guest favorite
Guest favorite
Cottage in Charlestown
Long Beach Cottage, (romantic couple’s getaway)
2 beds
2 beds
Jun 6 – 11
Jun 6 – 11
$500
night
$500 per night
4.98 out of 5 average rating, 49 reviews
4.98 (49)
Guest favorite
Guest favorite
Home in Rock Hall
Chesapeake Bay Retreat w/ Views!
4 beds
4 beds
May 12 – 17
May 12 – 17
$250
$139
night
$139 per night, originally $250
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Guest favorite
Guest favorite
Treehouse in Friendsville
The birdhouse
2 double beds
2 double beds
May 31 – Jun 5
May 31 – Jun 5
$158
night
$158 per night
4.93 out of 5 average rating, 113 reviews
4.93 (113)
Guest favorite
Guest favorite
Tiny home in Accident
Romantic Getaway In The Pines
1 king bed
1 king bed
May 12 – 17
May 12 – 17
$139
night
$139 per night
4.96 out of 5 average rating, 165 reviews
4.96 (165)
Guest favorite
Guest favorite
Guesthouse in Myersville
Spruce Run Cottage, Farm stay on Catoctin Mountain
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$95
night
$95 per night
4.93 out of 5 average rating, 189 reviews
4.93 (189)
Guest favorite
Guest favorite
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
1 double bed
1 double bed
Apr 21 – 26
Apr 21 – 26
$72
night
$72 per night
4.98 out of 5 average rating, 292 reviews
4.98 (292)
Guest favorite
Guest favorite
Houseboat in Arnold
Boho Luxe Floating Tiny Home with 360 Views
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
$206
$185
night
$185 per night, originally $206
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Tiny home in Solomons
“Cabana by the Bay”-tiny home on a pier!
1 double bed
1 double bed
Aug 4 – 9
Aug 4 – 9
$165
night
$165 per night
4.95 out of 5 average rating, 535 reviews
4.95 (535)
Guest favorite
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
1 queen bed
1 queen bed
Apr 30 – May 5
Apr 30 – May 5
$201
night
$201 per night
4.94 out of 5 average rating, 263 reviews
4.94 (263)
Guest favorite
Guest favorite
Cabin in Myersville
Sleepy Hollow Log Cabin
4 beds
4 beds
Apr 27 – May 2
Apr 27 – May 2
$150
night
$150 per night
4.98 out of 5 average rating, 60 reviews
4.98 (60)
Guest favorite
Guest favorite
Guesthouse in Stevensville
Waterfront Getaway - View of bay from your bed
1 queen bed
1 queen bed
Apr 24 – 29
Apr 24 – 29
$263
$238
night
$238 per night, originally $263
5.0 out of 5 average rating, 205 reviews
5.0 (205)
Guest favorite
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 21 – 26
Apr 21 – 26
$325
$290
night
$290 per night, originally $325
4.99 out of 5 average rating, 104 reviews
4.99 (104)
Guest favorite
Guest favorite
Apartment in Lexington Park
Adorable Waterfront Apartment Weekend Getaway
1 queen bed
1 queen bed
Sep 23 – 28
Sep 23 – 28
$90
night
$90 per night
5.0 out of 5 average rating, 313 reviews
5.0 (313)
Guest favorite
Guest favorite
Home in Myersville
The Crooked Cottage: a Cozy, Curated Escape
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$145
night
$145 per night
4.97 out of 5 average rating, 145 reviews
4.97 (145)
Guest favorite
Guest favorite
Chalet in Marriottsville
Renovated 1973 Aframe
3 beds
3 beds
May 27 – Jun 1
May 27 – Jun 1
$268
night
$268 per night
5.0 out of 5 average rating, 29 reviews
5.0 (29)
Guest favorite
Guest favorite
Chalet in Swanton
Ella Bella Chalet: Hot Tub, Stunning Views, Wi-Fi
6 beds
6 beds
Apr 21 – 26
Apr 21 – 26
$199
night
$199 per night
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Home in Scotland
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
5 beds
5 beds
May 5 – 10
May 5 – 10
$244
$217
night
$217 per night, originally $244
5.0 out of 5 average rating, 10 reviews
5.0 (10)
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