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, 274 reviewsWaterfront Cottage Near Herrington and North Beach
Jul 26 – Aug 2
Cottage in Oakland
4.95 out of 5 average rating, 185 reviewsPet-Friendly Cozy Home w/Hot Tub & Fire Pit
Jun 9 – 16
Cottage in Swanton
4.92 out of 5 average rating, 201 reviews*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
Apr 24 – May 1
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Jan 18 – 25
Cottage in Charlestown
4.98 out of 5 average rating, 59 reviewsLong Beach Cottage, (romantic couple’s getaway)
Dec 21 – 28
Cottage in Saint Leonard
4.98 out of 5 average rating, 95 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Oct 11 – 18
Cottage in North East
5.0 out of 5 average rating, 47 reviewsCozy Cottage on the Chesapeake with Hot Tub
Aug 24 – 31
Cottage in Annapolis
4.85 out of 5 average rating, 52 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Jul 10 – 17
Cottage rentals with a pool
Cottage in Berlin
4.99 out of 5 average rating, 120 reviewsBayfront Cottage w/ Amazing Views
Mar 25 – Apr 1
Cottage in Cambridge
4.98 out of 5 average rating, 109 reviewsChurch Creek - waterfront cottage & pool - private
Mar 2 – 9
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Oct 17 – 24
Cottage in Neavitt
4.69 out of 5 average rating, 16 reviewsGrandview - Cottage 1A, King Bed, Pool, Bay, WIFI
Jan 16 – 23
Cottage in Chestertown
4.93 out of 5 average rating, 27 reviewsChesapeake East Shore Chestertown, Pool & Dock
Oct 19 – 26
Cottage in Berlin
4.93 out of 5 average rating, 82 reviewsQuiet Retreat near Assateague Island
Jan 24 – 31
Cottage in Ocean Pines
5.0 out of 5 average rating, 19 reviews3-bedroom cottage in Ocean Pines
Mar 27 – Apr 3
Cottage in Ocean City
4.94 out of 5 average rating, 35 reviewsCasita de la Playa-2 Bikes, Pool & Assateague Pass
Oct 13 – 20
Cottage rentals with free parking
Cottage in Oakland
4.98 out of 5 average rating, 100 reviewsPet friendly-Cottage in the Woods
Dec 13 – 20
Cottage in Middletown
4.91 out of 5 average rating, 226 reviewsCharming "Cream of the Crop" Cape ~❤️of Middletown
Apr 3 – 10
Cottage in Rock Hall
4.96 out of 5 average rating, 135 reviewsThe Blissful Retreat @theblissfulretreat
Dec 29 – Jan 5
Cottage in Aberdeen
4.95 out of 5 average rating, 149 reviewsTranquil Carriage House*MCM *Country *Wildlife
Oct 28 – Nov 4
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Apr 27 – May 4
Cottage in Saint Michaels
4.98 out of 5 average rating, 428 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Nov 13 – 20
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
Feb 5 – 12
Cottage in Saint Michaels
4.98 out of 5 average rating, 177 reviewsThe Little Anchor Cottage, St. Michaels, MD
Mar 10 – 17
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