Cottage vacation rentals in Maryland
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Top-rated cottage rentals in Maryland
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Maryland cottage rentals
Cottage rentals with a hot tub
Cottage in North Beach
4.96 out of 5 average rating, 273 reviewsWaterfront Cottage Near Herrington and North Beach
Jul 26 – Aug 2
Cottage in Swanton
4.92 out of 5 average rating, 201 reviews*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
Feb 15 – 22
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Feb 16 – 23
Cottage in Oakland
4.95 out of 5 average rating, 185 reviewsPet-Friendly Cozy Home w/Hot Tub & Fire Pit
Jun 19 – 26
Cottage in Charlestown
4.98 out of 5 average rating, 55 reviewsLong Beach Cottage, (romantic couple’s getaway)
Oct 9 – 16
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Jun 27 – Jul 4
Cottage in North East
5.0 out of 5 average rating, 47 reviewsCozy Cottage on the Chesapeake with Hot Tub
Mar 14 – 21
Cottage in Annapolis
4.84 out of 5 average rating, 50 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Sep 15 – 22
Cottage rentals with a pool
Cottage in Berlin
4.99 out of 5 average rating, 119 reviewsBayfront Cottage w/ Amazing Views
Feb 20 – 27
Cottage in Cambridge
4.98 out of 5 average rating, 108 reviewsChurch Creek - waterfront cottage & pool - private
Jan 31 – Feb 7
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Oct 6 – 13
Cottage in Neavitt
4.69 out of 5 average rating, 16 reviewsGrandview - Cottage 1A, King Bed, Pool, Bay, WIFI
Nov 3 – 10
Cottage in Chestertown
4.92 out of 5 average rating, 26 reviewsChesapeake East Shore Chestertown, Pool & Dock
Sep 7 – 14
Cottage in Berlin
4.93 out of 5 average rating, 82 reviewsQuiet Retreat near Assateague Island
Dec 25 – Jan 1
Cottage in Ocean Pines
5.0 out of 5 average rating, 19 reviews3-bedroom cottage in Ocean Pines
Apr 1 – 8
Cottage in Ocean City
4.94 out of 5 average rating, 35 reviewsCasita de la Playa-2 Bikes, Pool & State Park Pass
Jun 8 – 15
Cottage rentals with free parking
Cottage in Westover
4.99 out of 5 average rating, 181 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Dec 19 – 26
Cottage in Leonardtown
4.91 out of 5 average rating, 149 reviewsPotomac Vista Cottage at Little Pond
Sep 27 – Oct 4
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
Oct 25 – Nov 1
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Oct 4 – 11
Cottage in Middletown
4.92 out of 5 average rating, 224 reviewsCharming "Cream of the Crop" Cape ~❤️of Middletown
Feb 4 – 11
Cottage in Aberdeen
4.95 out of 5 average rating, 148 reviewsTranquil Carriage House*MCM *Country *Wildlife
Apr 1 – 8
Cottage in Rock Hall
4.95 out of 5 average rating, 133 reviewsThe Blissful Retreat @theblissfulretreat
Nov 28 – Dec 5
Cottage in Leonardtown
4.93 out of 5 average rating, 193 reviewsPotomac River Freedom Cottage
Oct 1 – 8
Destinations to explore
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