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 Saint Michaels cottage rentals
Cottage rentals with a hot tub
Cottage in Reedville
4.9 out of 5 average rating, 161 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
2–9 Nov
Cottage in Reedville
4.91 out of 5 average rating, 143 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
12–19 Sep
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
16–23 Feb
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
6–13 Oct
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
27 Jun – 4 Jul
Cottage in Annapolis
4.84 out of 5 average rating, 50 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
15–22 Sep
Cottage in Heathsville
4.9 out of 5 average rating, 71 reviewsWaterfront Cottage w Private Beach & Hot Tub
23–30 Mar
Cottage in Montross
4.93 out of 5 average rating, 57 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
11–18 Jul
Pet-friendly cottage rentals
Cottage in Annapolis
4.94 out of 5 average rating, 314 reviewsWright’s Cottage, Pets Welcome!
29 Jul – 5 Aug
Cottage in Deal Island
4.93 out of 5 average rating, 119 reviewsWater View Cottage
1–8 Oct
Cottage in Kinsale
4.95 out of 5 average rating, 195 reviewsGreat little cottage with a "Rivah" view
13–20 Apr
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
18–25 Dec
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 Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
4–11 Oct
Cottage in Annapolis
4.97 out of 5 average rating, 116 reviewsWaterfront farm retreat for vacation & telework
18–25 Mar
Cottage in North Beach
4.97 out of 5 average rating, 100 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
1–8 Jan
Private cottage rentals
Cottage in Leonardtown
4.97 out of 5 average rating, 126 reviewsBeach Front and 'Perfectly Placed'
21–28 Sep
Cottage in Chincoteague Island
4.97 out of 5 average rating, 330 reviewsOnce Upon A Tide
4–11 Feb
Cottage in Tracys Landing
4.9 out of 5 average rating, 337 reviewsCharming Waterfront on Chesapeake Bay
8–15 Jan
Cottage in Stevensville
4.94 out of 5 average rating, 131 reviewsCottage on the Bay - Kent Island
2–9 Oct
Cottage in Smith Island
4.97 out of 5 average rating, 184 reviewsLevering Creek Cottage with Private Docking
10–17 Feb
Cottage in Rock Hall
4.95 out of 5 average rating, 133 reviewsThe Blissful Retreat @theblissfulretreat
28 Nov – 5 Dec
Cottage in Leonardtown
4.91 out of 5 average rating, 149 reviewsPotomac Vista Cottage at Little Pond
27 Sep – 4 Oct
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
25 Oct – 1 Nov
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