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 free parking
Cottage in Annapolis
4.96 out of 5 average rating, 340 reviewsRelaxing Water Views - Mill Creek Cottage
Cottage in Leonardtown
4.91 out of 5 average rating, 150 reviewsPotomac Vista Cottage at Little Pond
Cottage in Oakland
4.98 out of 5 average rating, 101 reviewsPet friendly-Cottage in the Woods
Cottage in Rock Hall
4.96 out of 5 average rating, 135 reviewsThe Blissful Retreat @theblissfulretreat
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Cottage in Middletown
4.91 out of 5 average rating, 226 reviewsCharming "Cream of the Crop" Cape ~❤️of Middletown
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
Cottage in Saint Michaels
4.98 out of 5 average rating, 429 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Cottage rentals with a hot tub
Cottage in Swanton
4.92 out of 5 average rating, 201 reviews*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
Cottage in Oakland
4.95 out of 5 average rating, 185 reviewsPet-Friendly Cozy Home w/Hot Tub & Fire Pit
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Cottage in Charlestown
4.98 out of 5 average rating, 60 reviewsLong Beach Cottage, (romantic couple’s getaway)
Cottage in Saint Leonard
4.98 out of 5 average rating, 95 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Cottage in North East
5.0 out of 5 average rating, 47 reviewsCozy Cottage on the Chesapeake with Hot Tub
Cottage in Annapolis
4.85 out of 5 average rating, 53 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Cottage in Bryans Road
4.89 out of 5 average rating, 76 reviewsThe Potomac House: 13 acre riverfront property
Cottage rentals with a pool
Cottage in Cambridge
4.98 out of 5 average rating, 109 reviewsChurch Creek - waterfront cottage & pool - private
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Cottage in Neavitt
4.69 out of 5 average rating, 16 reviewsGrandview - Cottage 1A, King Bed, Pool, Bay, WIFI
Cottage in Chestertown
4.93 out of 5 average rating, 27 reviewsChesapeake East Shore Chestertown, Pool & Dock
Cottage in Berlin
4.93 out of 5 average rating, 82 reviewsQuiet Retreat near Assateague Island
Cottage in Ocean Pines
5.0 out of 5 average rating, 20 reviews3-bedroom cottage in Ocean Pines
Cottage in Ocean City
4.94 out of 5 average rating, 35 reviewsCasita de la Playa-2 Bikes, Pool & Assateague Pass
Cottage in Riva
4.95 out of 5 average rating, 22 reviewsCozy Cottage on the South River
Destinations to explore
- Rentals with beach access Maryland
- Beach house rentals Maryland
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- Bungalow rentals Maryland
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- Bed and breakfasts Maryland
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- Rentals with a home theater Maryland
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- Farmstay rentals Maryland
- Monthly Rentals Maryland
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- Condo rentals Maryland
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- Wheelchair accessible rentals Maryland
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