Cottage holiday rentals in Southern Maryland
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Top-rated cottage rentals in Southern 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 Southern Maryland
Cottage rentals with a hot tub
Cottage in Reedville
4.91 out of 5 average rating, 143 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
29 Aug – 5 Sep
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
2–9 Apr
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
29 Nov – 6 Dec
Cottage in Heathsville
4.9 out of 5 average rating, 72 reviewsWaterfront Cottage w Private Beach & Hot Tub
11–18 Nov
Cottage in Saint Leonard
4.98 out of 5 average rating, 95 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
6–13 Feb
Cottage in Montross
4.91 out of 5 average rating, 58 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
31 Jul – 7 Aug
Cottage in Heathsville
4.89 out of 5 average rating, 18 reviewsWaterfront Heathsville Cottage w/ Dock & Hot Tub!
8–15 Sep
Cottage in Chesapeake Beach
4.5 out of 5 average rating, 18 reviewsAdorable Beach Cottage w/ Hot Tub & Tropical Bar!
1–8 Dec
Pet-friendly cottage rentals
Cottage in Reedville
4.95 out of 5 average rating, 114 reviewsBull Neck Cottage
25 May – 1 Jun
Cottage in Saint Michaels
4.98 out of 5 average rating, 177 reviewsThe Little Anchor Cottage, St. Michaels, MD
29 Jul – 5 Aug
Cottage in Fredericksburg
4.85 out of 5 average rating, 359 reviewsRappahannock River Cottage, Near I-95! Sleeps 6!
26 Mar – 2 Apr
Cottage in North Beach
4.97 out of 5 average rating, 103 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
29 Jan – 5 Feb
Cottage in Neavitt
4.9 out of 5 average rating, 124 reviewsThe Middle Point Cottage at Saint Michaels
11–18 Jul
Cottage in Tall Timbers
4.9 out of 5 average rating, 106 reviewsSunsets on Potomac, Woodland Cottage with Views
29 Sep – 6 Oct
Cottage in Deale
4.89 out of 5 average rating, 148 reviewsRockhold Creek Cottage
17–24 Feb
Cottage in Deale
4.81 out of 5 average rating, 167 reviewsWatrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
24–31 Jan
Private cottage rentals
Cottage in Saint Michaels
4.98 out of 5 average rating, 428 reviewsSt. Michaels-Historic Dist. Margaret Wells House
13–20 Nov
Cottage in Tracys Landing
4.9 out of 5 average rating, 338 reviewsCharming Waterfront on Chesapeake Bay
12–19 Oct
Cottage in Colonial Beach
4.83 out of 5 average rating, 143 reviewsSUPERB BEACH COTTAGE- Waterview, firepit, porch!
20–27 Aug
Cottage in Broomes Island
4.9 out of 5 average rating, 122 reviewsGorgeous Waterfront Home!
20–27 Dec
Cottage in Reedville
4.9 out of 5 average rating, 173 reviewsChesapeake Bay Beach Cottage
7–14 Aug
Cottage in Wittman
4.9 out of 5 average rating, 136 reviews"Wittman Cottage"
10–17 Feb
Cottage in Stevensville
4.94 out of 5 average rating, 132 reviewsCottage on the Bay - Kent Island
9–16 Oct
Cottage in Hague
5.0 out of 5 average rating, 83 reviewsPotomac River cheerful cottage
5–12 Oct
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Richmond Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Charlottesville Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Cottage rentals Maryland
- Cottage rentals Maryland
- Monthly Rentals Southern Maryland
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- Rentals with a kayak Southern Maryland
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