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
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Popular amenities for cottage rentals in Saint Michaels
Cottage rentals with a hot tub
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
28 Jan – 4 Feb
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
30 Jan – 6 Feb
Cottage in Bryans Road
4.89 out of 5 average rating, 75 reviewsThe Potomac House: 13 acre riverfront property
29 Sep – 6 Oct
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
18–25 Apr
Cottage in Montross
4.91 out of 5 average rating, 58 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
18–25 Mar
Cottage in Annapolis
4.84 out of 5 average rating, 51 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
5–12 Dec
Cottage in Chesapeake Beach
4.5 out of 5 average rating, 18 reviewsAdorable Beach Cottage w/ Hot Tub & Tropical Bar!
23 Feb – 2 Mar
Cottage in Baltimore
4.41 out of 5 average rating, 39 reviewsCozy Cottage Garden Getaway
25 Jun – 2 Jul
Pet-friendly cottage rentals
Cottage in Westover
4.99 out of 5 average rating, 182 reviewsRumbley Cottage on the Tangier Sound-Private Beach
19–26 Jan
Cottage in Deal Island
4.93 out of 5 average rating, 120 reviewsWater View Cottage
25 Oct – 1 Nov
Cottage in North Beach
4.95 out of 5 average rating, 125 reviewsClub Carp North Beach - Steps to the Bay!
30 Aug – 6 Sep
Cottage in Kinsale
4.95 out of 5 average rating, 196 reviewsGreat little cottage with a "Rivah" view
14–21 Sep
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
18–25 Dec
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
16–23 Nov
Cottage in Annapolis
4.97 out of 5 average rating, 116 reviewsWaterfront farm retreat for vacation & telework
13–20 Nov
Cottage in Pasadena
4.97 out of 5 average rating, 158 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
12–19 Jun
Private cottage rentals
Cottage in Tracys Landing
4.9 out of 5 average rating, 338 reviewsCharming Waterfront on Chesapeake Bay
12–19 Sep
Cottage in Stevensville
4.94 out of 5 average rating, 132 reviewsCottage on the Bay - Kent Island
3–10 Oct
Cottage in Smith Island
4.97 out of 5 average rating, 185 reviewsLevering Creek Cottage with Private Docking
17–24 Jun
Cottage in Leonardtown
4.91 out of 5 average rating, 150 reviewsPotomac Vista Cottage at Little Pond
4–11 Feb
Cottage in Rock Hall
4.96 out of 5 average rating, 134 reviewsThe Blissful Retreat @theblissfulretreat
6–13 Apr
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
9–16 Dec
Cottage in Deale
4.95 out of 5 average rating, 139 reviewsChesapeake Bay Cottage
26 Sep – 3 Oct
Cottage in Leonardtown
4.93 out of 5 average rating, 194 reviewsPotomac River Freedom Cottage
11–18 Sep
Destinations to explore
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