Cottage holiday rentals in Saint Michaels
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Top-rated cottage rentals in Saint Michaels
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 Saint Michaels cottage rentals
Cottage rentals with a hot tub
Cottage in Easton
5.0 out of 5 average rating, 84 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Cottage in Montross
4.92 out of 5 average rating, 61 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Cottage in Bryans Road
4.9 out of 5 average rating, 79 reviewsThe Potomac House: 13 acre riverfront property
Cottage in Annapolis
4.85 out of 5 average rating, 54 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Cottage in Lusby
New place to stayBayHollow: HOT TUB with treetop views
Cottage in Chesapeake Beach
4.5 out of 5 average rating, 18 reviewsAdorable Beach Cottage w/ Hot Tub & Tropical Bar!
Cottage in Marion Station
4.48 out of 5 average rating, 21 reviewsYear Round Playground - Rare Rustic-Modern Getaway
Pet-friendly cottage rentals
Cottage in Woodbine
4.91 out of 5 average rating, 126 reviewsGate House
Cottage in Montross
4.97 out of 5 average rating, 101 reviewsNewly Renovated 2BR Waterfront Cottage with Dock
Cottage in Deal Island
4.93 out of 5 average rating, 123 reviewsWater View Cottage
Cottage in Westover
4.92 out of 5 average rating, 146 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
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, 130 reviewsClub Carp North Beach - Steps to the Bay!
Cottage in Colonial Beach
4.98 out of 5 average rating, 126 reviewsRiver view dog friendly YOLO Beach House
Cottage in Pasadena
4.97 out of 5 average rating, 159 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
Private cottage rentals
Cottage in Tracys Landing
4.9 out of 5 average rating, 340 reviewsCharming Waterfront on Chesapeake Bay
Cottage in Rock Hall
4.96 out of 5 average rating, 137 reviewsThe Blissful Retreat @theblissfulretreat
Cottage in Stevensville
4.94 out of 5 average rating, 134 reviewsCottage on the Bay - Kent Island
Cottage in Deale
4.95 out of 5 average rating, 141 reviewsChesapeake Bay Cottage
Cottage in Leonardtown
4.93 out of 5 average rating, 128 reviewsBreton Breeze
Cottage in Leonardtown
4.93 out of 5 average rating, 196 reviewsPotomac River Freedom Cottage
Cottage in Rock Hall
4.99 out of 5 average rating, 103 reviewsCottage by the Bay in Rock Hall, MD
Cottage in Deale
4.81 out of 5 average rating, 167 reviewsWatrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
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