Cottage vacation 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.
Vacation 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 pool
Cottage in Neavitt
4.69 out of 5 average rating, 16 reviewsGrandview - Cottage 1A, King Bed, Pool, Bay, WIFI
Mar 23 – 30
Cottage in Chestertown
4.92 out of 5 average rating, 26 reviewsChesapeake East Shore Chestertown, Pool & Dock
Apr 15 – 22
Cottage in Heathsville
4.83 out of 5 average rating, 58 reviewsRiverfront Retreat with PRIVATE POOL and BEACH!!
Sep 29 – Oct 6
Cottage in Montross
5.0 out of 5 average rating, 49 reviewsPaddler's Place: waterfront cottage with dock
Dec 24 – 31
Cottage in Montross
4.94 out of 5 average rating, 17 reviewsHarbor Cottage
Oct 17 – 24
Cottage in Chincoteague
4.87 out of 5 average rating, 31 reviewsHoliday Cottages-Mako Cottage
Jan 3 – 10
Cottage in Trappe
4.83 out of 5 average rating, 18 reviewsPrivate Waterfront Cottage on Bolingbroke Creek
Oct 8 – 15
Cottage in Arnold
5.0 out of 5 average rating, 28 reviewsRare Find, 5 Stars, Heated Salt Water Pool!
Mar 4 – 11
Cottage rentals with a hot tub
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Feb 14 – 21
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Mar 18 – 25
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Oct 13 – 20
Cottage in Heathsville
4.9 out of 5 average rating, 71 reviewsWaterfront Cottage w Private Beach & Hot Tub
Dec 30 – Jan 6
Cottage in Annapolis
4.84 out of 5 average rating, 51 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Sep 26 – Oct 3
Cottage in Bryans Road
4.89 out of 5 average rating, 75 reviewsThe Potomac House: 13 acre riverfront property
Jun 4 – 11
Cottage in Montross
4.91 out of 5 average rating, 58 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Nov 20 – 27
Cottage in Annapolis
5.0 out of 5 average rating, 7 reviewsWaterfront Available 2024 Commissioning Week
Jan 28 – Feb 4
Pet-friendly cottage rentals
Cottage in Annapolis
4.94 out of 5 average rating, 314 reviewsWright’s Cottage, Pets Welcome!
May 16 – 23
Cottage in Deal Island
4.93 out of 5 average rating, 120 reviewsWater View Cottage
Oct 27 – Nov 3
Cottage in North Beach
4.95 out of 5 average rating, 125 reviewsClub Carp North Beach - Steps to the Bay!
Aug 30 – Sep 6
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
Sep 19 – 26
Cottage in Kinsale
4.95 out of 5 average rating, 196 reviewsGreat little cottage with a "Rivah" view
Jan 27 – Feb 3
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Nov 16 – 23
Cottage in Annapolis
4.97 out of 5 average rating, 116 reviewsWaterfront farm retreat for vacation & telework
Feb 4 – 11
Cottage in Pasadena
4.97 out of 5 average rating, 158 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
Jun 14 – 21
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