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 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
26 July – 2 Aug
Cottage in McHenry
4.97 out of 5 average rating, 109 reviewsCozy getaway w/ Theater, Hot Tub, and Scenic Views
29 July – 5 Aug
Cottage in Swanton
4.92 out of 5 average rating, 201 reviews*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit
6 – 13 Dec
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
22 – 29 Aug
Cottage in Oakland
4.95 out of 5 average rating, 185 reviewsPet-Friendly Cozy Home w/Hot Tub & Fire Pit
27 Dec – 3 Jan
Cottage in Charlestown
4.98 out of 5 average rating, 53 reviewsLong Beach Cottage, (romantic couple’s getaway)
1 – 8 Jan
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
13 – 20 Apr
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub & Firepit
23 – 30 Apr
Pet-friendly cottage rentals
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
30 Mar – 6 Apr
Cottage in Middletown
4.91 out of 5 average rating, 222 reviewsCharming "Cream of the Crop" Cape ~❤️of Middletown
4 – 11 June
Cottage in Pasadena
4.97 out of 5 average rating, 158 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
14 – 21 June
Cottage in Saint Michaels
4.98 out of 5 average rating, 176 reviewsThe Little Anchor Cottage, St. Michaels, MD
15 – 22 Feb
Cottage in Annapolis
4.97 out of 5 average rating, 115 reviewsWaterfront farm retreat for vacation & telework
11 – 18 Mar
Cottage in Sharpsburg
4.86 out of 5 average rating, 101 reviewsPeaceful River House on Potomac- King Size Bed
7 – 14 Oct
Cottage in North Beach
4.95 out of 5 average rating, 125 reviewsClub Carp North Beach - Steps to the Bay!
2 – 9 Dec
Cottage in North Beach
4.97 out of 5 average rating, 100 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
8 – 15 Apr
Private cottage rentals
Cottage in Port Deposit
4.91 out of 5 average rating, 172 reviewsThe River Cottage
9 – 16 Jan
Cottage in Leonardtown
4.91 out of 5 average rating, 149 reviewsPotomac Vista Cottage at Little Pond
3 – 10 Oct
Cottage in Cambridge
4.98 out of 5 average rating, 108 reviewsChurch Creek - waterfront cottage & pool - private
15 – 22 Mar
Cottage in Aberdeen
4.95 out of 5 average rating, 148 reviewsTranquil Carriage House*MCM *Country *Wildlife
10 – 17 Jan
Cottage in Leonardtown
4.93 out of 5 average rating, 193 reviewsPotomac River Freedom Cottage
30 Sept – 7 Oct
Cottage in Smith Island
4.97 out of 5 average rating, 184 reviewsLevering Creek Cottage with Private Docking
18 – 25 Jan
Cottage in Saint Michaels
4.98 out of 5 average rating, 425 reviewsSt. Michaels-Historic Dist. Margaret Wells House
9 – 16 Mar
Cottage in Rock Hall
4.95 out of 5 average rating, 133 reviewsThe Blissful Retreat @theblissfulretreat
24 Apr – 1 May
Destinations to explore
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