
Cottage vacation rentals in Annapolis
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Top-rated cottage rentals in Annapolis
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 Annapolis cottage rentals
Cottage rentals with free parking

Cozy Off-street Cottage Maryland

Sailor's Cottage - Private Waterfront

The Blue Crab Beach House - Free beach passes

Rare Find 5 Star, No Cleaning fee, Salt Water Pool

Newly Renovated Summer Paradise-Pool-Tennis-Garden

Wonderful Cottage Nestled On Chesapeake Bay

The Little House of Rockaway Beach, Maryland

Duck Cove Waterfront Cottage
Cottage rentals with a hot tub

Waterfront cottage w/hot tub/ gated/ pier/ firepit

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Nautical Vibe Walk 2 Harbor Pubs USNA

Waterfront Cottage Near Herrington and North Beach

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Pet-friendly cottage rentals

The Little Anchor Cottage, St. Michaels, MD

Cottage with Modern Updates - Walk to Waterfront!

Perfect St. Michaels Getaway

Waterfront River Cottage for 2, Dog-friendly

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Rockhold Creek Cottage

THE PRINCE COTTAGE WITH PRIVATE PARKING GARAGE!!!

Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet F
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- Nationals Park
- Betterton Beach
- The White House
- National Mall
- Georgetown University
- Hampden
- National Museum of African American History and Culture
- Oriole Park at Camden Yards
- Smithsonian National Museum of Natural History
- District Wharf
- Six Flags America
- Sandy Point State Park
- Patterson Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- M&T Bank Stadium
- National Air and Space Museum
- Smithsonian American Art Museum
- National Harbor
- Lincoln Park
- Great Falls Park
- Meridian Hill Park
- Congressional Country Club
- Family travel hub Tips and inspiration
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- 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