Cottage vacation rentals in Saint Michaels
Find and book unique cottages on Airbnb
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 20 – 27
Cottage in Chestertown
4.93 out of 5 average rating, 27 reviewsChesapeake East Shore Chestertown, Pool & Dock
Apr 16 – 23
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
Nov 20 – 27
Cottage in Montross
4.94 out of 5 average rating, 17 reviewsHarbor Cottage
Jan 18 – 25
Cottage in Chincoteague
4.87 out of 5 average rating, 31 reviewsHoliday Cottages-Mako Cottage
Mar 21 – 28
Cottage in Trappe
4.83 out of 5 average rating, 18 reviewsPrivate Waterfront Cottage on Bolingbroke Creek
Oct 9 – 16
Cottage in Arnold
5.0 out of 5 average rating, 28 reviewsRare Find, 5 Stars, Heated Salt Water Pool!
Mar 20 – 27
Cottage rentals with a hot tub
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Mar 27 – Apr 3
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Apr 20 – 27
Cottage in Saint Leonard
4.98 out of 5 average rating, 93 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Oct 8 – 15
Cottage in Heathsville
4.9 out of 5 average rating, 71 reviewsWaterfront Cottage w Private Beach & Hot Tub
Nov 7 – 14
Cottage in Annapolis
4.84 out of 5 average rating, 51 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Dec 15 – 22
Cottage in Bryans Road
4.89 out of 5 average rating, 75 reviewsThe Potomac House: 13 acre riverfront property
Jun 14 – 21
Cottage in Montross
4.91 out of 5 average rating, 58 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Feb 7 – 14
Cottage in Annapolis
5.0 out of 5 average rating, 7 reviewsWaterfront Available 2024 Commissioning Week
Feb 23 – Mar 2
Pet-friendly cottage rentals
Cottage in Annapolis
4.94 out of 5 average rating, 315 reviewsWright’s Cottage, Pets Welcome!
Jul 22 – 29
Cottage in Deal Island
4.93 out of 5 average rating, 120 reviewsWater View Cottage
Nov 9 – 16
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 Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
Nov 7 – 14
Cottage in Kinsale
4.95 out of 5 average rating, 196 reviewsGreat little cottage with a "Rivah" view
Oct 4 – 11
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Feb 23 – Mar 2
Cottage in Annapolis
4.97 out of 5 average rating, 117 reviewsWaterfront farm retreat for vacation & telework
Nov 27 – Dec 4
Cottage in North Beach
4.97 out of 5 average rating, 102 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
Feb 15 – 22
Destinations to explore
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Cape May Vacation rentals
- Wildwood Vacation rentals
- Rehoboth Beach Vacation rentals
- Arlington Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes