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
Dec 14 – 21
Cottage in Chestertown
4.93 out of 5 average rating, 27 reviewsChesapeake East Shore Chestertown, Pool & Dock
Apr 17 – 24
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
Jan 19 – 26
Cottage in Montross
4.94 out of 5 average rating, 18 reviewsHarbor Cottage
Oct 8 – 15
Cottage in Trappe
4.83 out of 5 average rating, 18 reviewsPrivate Waterfront Cottage on Bolingbroke Creek
Oct 24 – 31
Cottage in Arnold
5.0 out of 5 average rating, 28 reviewsRare Find, 5 Stars, Heated Salt Water Pool!
Mar 5 – 12
Cottage in Saint Michaels
Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet F
Apr 24 – May 1
Cottage rentals with a hot tub
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Apr 22 – 29
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Oct 16 – 23
Cottage in Saint Leonard
4.98 out of 5 average rating, 93 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Feb 3 – 10
Cottage in Heathsville
4.9 out of 5 average rating, 71 reviewsWaterfront Cottage w Private Beach & Hot Tub
Dec 2 – 9
Cottage in Annapolis
4.84 out of 5 average rating, 51 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Dec 9 – 16
Cottage in Bryans Road
4.89 out of 5 average rating, 75 reviewsThe Potomac House: 13 acre riverfront property
Oct 3 – 10
Cottage in Montross
4.91 out of 5 average rating, 58 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Mar 7 – 14
Cottage in Annapolis
5.0 out of 5 average rating, 7 reviewsWaterfront Available 2024 Commissioning Week
Oct 18 – 25
Pet-friendly cottage rentals
Cottage in North Beach
4.95 out of 5 average rating, 125 reviewsClub Carp North Beach - Steps to the Bay!
Oct 23 – 30
Cottage in Deal Island
4.93 out of 5 average rating, 120 reviewsWater View Cottage
Oct 24 – 31
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
Dec 13 – 20
Cottage in Kinsale
4.95 out of 5 average rating, 196 reviewsGreat little cottage with a "Rivah" view
Oct 21 – 28
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Oct 20 – 27
Cottage in Annapolis
4.97 out of 5 average rating, 117 reviewsWaterfront farm retreat for vacation & telework
Dec 29 – Jan 5
Cottage in Pasadena
4.97 out of 5 average rating, 158 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
Jun 16 – 23
Cottage in North Beach
4.97 out of 5 average rating, 102 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
Jan 29 – Feb 5
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