Cottage holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Maryland
Cottage rentals with a hot tub
Cottage in North Beach
4.96 out of 5 average rating, 278 reviewsWaterfront Cottage Near Herrington and North Beach
Cottage in Swanton
4.92 out of 5 average rating, 203 reviews*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
Cottage in Oakland
4.95 out of 5 average rating, 191 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
4.97 out of 5 average rating, 67 reviewsLong Beach Cottage, (romantic couple’s getaway)
Cottage in Easton
5.0 out of 5 average rating, 84 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Cottage in Annapolis
4.85 out of 5 average rating, 54 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Cottage in North East
5.0 out of 5 average rating, 47 reviewsCozy Cottage on the Chesapeake with Hot Tub
Pet-friendly cottage rentals
Cottage in Westover
4.93 out of 5 average rating, 147 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Cottage in Middletown
4.91 out of 5 average rating, 229 reviewsCharming "Cream of the Crop" Cape ~❤️of Middletown
Cottage in Oakland
4.97 out of 5 average rating, 105 reviewsPet friendly-Cottage in the Woods
Cottage in Saint Michaels
4.98 out of 5 average rating, 186 reviewsThe Little Anchor Cottage, St. Michaels, MD
Cottage in Pasadena
4.97 out of 5 average rating, 159 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
Cottage in Sharpsburg
4.86 out of 5 average rating, 104 reviewsPeaceful River House on Potomac- King Size Bed
Cottage in Annapolis
4.97 out of 5 average rating, 119 reviewsWaterfront farm retreat for vacation & telework
Cottage in North Beach
4.94 out of 5 average rating, 131 reviewsClub Carp North Beach - Steps to the Bay!
Private cottage rentals
Cottage in Cambridge
4.98 out of 5 average rating, 114 reviewsChurch Creek - waterfront cottage & pool - private
Cottage in Leonardtown
4.93 out of 5 average rating, 128 reviewsBreton Breeze
Cottage in Sharpsburg
4.96 out of 5 average rating, 160 reviewsLock Keepers Cottage on C&O Canal/Potomac River
Cottage in Aberdeen
4.95 out of 5 average rating, 154 reviewsTranquil Carriage House*MCM *Country *Wildlife
Cottage in Rock Hall
4.96 out of 5 average rating, 139 reviewsThe Blissful Retreat @theblissfulretreat
Cottage in Smith Island
4.97 out of 5 average rating, 192 reviewsLevering Creek Cottage with Private Docking
Cottage in Tracys Landing
4.89 out of 5 average rating, 342 reviewsCharming Waterfront on Chesapeake Bay
Cottage in Leonardtown
4.93 out of 5 average rating, 196 reviewsPotomac River Freedom Cottage
Destinations to explore
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