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 Bryans Road
4.89 out of 5 average rating, 75 reviewsThe Potomac House: 13 acre riverfront property
14 – 21 June
Cottage in Montross
4.91 out of 5 average rating, 58 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
15 – 22 June
Cottage in Scotland
4.93 out of 5 average rating, 15 reviewsHays Beach House - Hot Tub - Private Beach
2 – 9 June
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
24 Nov – 1 Dec
Cottage in Riva
4.95 out of 5 average rating, 22 reviewsCozy Cottage on the South River
16 – 23 Oct
Cottage in Annapolis
4.84 out of 5 average rating, 51 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
11 – 18 Dec
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
24 June – 1 July
Cottage in Chesapeake Beach
4.5 out of 5 average rating, 18 reviewsAdorable Beach Cottage w/ Hot Tub & Tropical Bar!
10 – 17 Mar
Pet-friendly cottage rentals
Cottage in Deal Island
4.93 out of 5 average rating, 120 reviewsWater View Cottage
1 – 8 Jan
Cottage in Westover
4.99 out of 5 average rating, 182 reviewsRumbley Cottage on the Tangier Sound-Private Beach
7 – 14 Apr
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
26 Dec – 2 Jan
Cottage in North Beach
4.95 out of 5 average rating, 125 reviewsClub Carp North Beach - Steps to the Bay!
30 Aug – 6 Sept
Cottage in Kinsale
4.95 out of 5 average rating, 196 reviewsGreat little cottage with a "Rivah" view
26 Nov – 3 Dec
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
26 Oct – 2 Nov
Cottage in Colonial Beach
4.91 out of 5 average rating, 116 reviewsShore Cottage Getaway - Water access
8 – 15 Jan
Cottage in Annapolis
4.97 out of 5 average rating, 116 reviewsWaterfront farm retreat for vacation & telework
20 – 27 Apr
Private cottage rentals
Cottage in Tracys Landing
4.9 out of 5 average rating, 337 reviewsCharming Waterfront on Chesapeake Bay
26 Sept – 3 Oct
Cottage in Stevensville
4.94 out of 5 average rating, 132 reviewsCottage on the Bay - Kent Island
3 – 10 Oct
Cottage in Leonardtown
4.91 out of 5 average rating, 150 reviewsPotomac Vista Cottage at Little Pond
23 – 30 Mar
Cottage in Rock Hall
4.96 out of 5 average rating, 134 reviewsThe Blissful Retreat @theblissfulretreat
17 – 24 Oct
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
8 – 15 Dec
Cottage in Deale
4.95 out of 5 average rating, 139 reviewsChesapeake Bay Cottage
2 – 9 Nov
Cottage in Leonardtown
4.93 out of 5 average rating, 193 reviewsPotomac River Freedom Cottage
10 – 17 Sept
Cottage in Rock Hall
4.99 out of 5 average rating, 102 reviewsCottage by the Bay in Rock Hall, MD
2 – 9 Oct
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