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Search results; 164 places in Annapolis

Guest favorite
Guest suite in Arnold
Old Bay Bungalow
2 beds
Apr 28 – May 3
4.96 out of 5 average rating, 563 reviews
Superhost
Home in Annapolis
Heart of Eastport 4 bedroom Modern Craftsman!
6 beds
May 5 – 10
4.77 out of 5 average rating, 87 reviews
Guest favorite
Guesthouse in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 queen bed
Apr 29 – May 4
4.97 out of 5 average rating, 155 reviews
Superhost
Home in Annapolis
Hidden Gem! 6 Guests • 3 Bed • 2 Baths
3 beds
May 6 – 11
Guest favorite
Room in Crofton
Stay with TammyRealtor,
Lovely Suite with a Nice Garden View
Apr 27 – May 2
4.84 out of 5 average rating, 270 reviews
Guest favorite
Room in Annapolis
Stay with MarshaHosting for 12 years,
Cozy private room in Annapolis home
Apr 21 – 26
4.83 out of 5 average rating, 416 reviews
Guest favorite
Room in Arnold
Stay with CindiRemodeling,
Magothy View Bed & Breakfast
Apr 30 – May 5
4.99 out of 5 average rating, 217 reviews
Guest favorite
Apartment in Crownsville
“River Sweet" Private Apartment
1 queen bed
Apr 29 – May 4
4.98 out of 5 average rating, 163 reviews
Guest favorite
Room in Annapolis
Stay with JenniferHosting for 6 years,
Chesapeake Mornings
Jun 1 – 6
4.96 out of 5 average rating, 460 reviews
Superhost
Guesthouse in Annapolis
The Barn on Howards Cove with a Pier for your boat
4 beds
Jun 24 – 29
Guest favorite
Room in Annapolis
Stay with CathyRetired,
Howard's Cove Retreat
May 8 – 13
4.91 out of 5 average rating, 487 reviews
Room in Annapolis
Stay with Brice MerlinHosting for 6 years,
Quiet-Home Annapolis
Apr 21 – 26
4.85 out of 5 average rating, 95 reviews
Guest favorite
Apartment in Crownsville
Private Apartment @ Hidden View Farm
1 queen bed
Apr 20 – 25
5.0 out of 5 average rating, 31 reviews
Boutique hotel in Annapolis
Cozy Suite Near Annapolis Town Center! 5 Min Drive
2 queen beds
Apr 28 – May 3
New place to stay
Superhost
Cottage in Arnold
Sail, Power Boat into Deep Creek Arnold Getaway
2 beds
Apr 20 – 25
4.76 out of 5 average rating, 46 reviews
Room in Annapolis
Stay with Mathew
Stay right on Main Street Annapolis! Private room with Queen-sized bed and bath.
Apr 21 – 26
4.65 out of 5 average rating, 37 reviews
Guest favorite
Guest suite in Chesapeake Beach
Nice Guest Suite at Chesapeake Bay
1 bed
Apr 20 – 25
4.95 out of 5 average rating, 82 reviews
Guest favorite
Room in Stevensville
Stay with LindySales,
Rustic & Elegant Private Bed & Bath
May 5 – 10
4.97 out of 5 average rating, 226 reviews