
Holiday rentals in Annapolis
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Top-rated holiday rentals in Annapolis
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Holiday rentals for every style
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Popular amenities for Annapolis holiday rentals
Other great holiday rentals in Annapolis
Top guest favourite

Home in Annapolis
4.99 out of 5 average rating, 96 reviewsNautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
Top guest favourite

Guest suite in Annapolis
4.96 out of 5 average rating, 76 reviewsBay View Studio Apartment
Guest favourite

Flat in Annapolis
4.88 out of 5 average rating, 17 reviewsNaptown’s Nauti Flat
Superhost

Flat in Annapolis
4.83 out of 5 average rating, 69 reviewsLovely 1 bedroom apartment in downtown Annapolis
Guest favourite

Home in Annapolis
4.94 out of 5 average rating, 34 reviewsHistoric Home in Annapolis
Top guest favourite

Home in Annapolis
4.96 out of 5 average rating, 46 reviewsCute Downtwn Townhouse *Onsite Parking* & Patio!
Top guest favourite

Home in Annapolis
5 out of 5 average rating, 7 reviewsHistoric + Modern Home | Just Steps to Waterfront
Guest favourite

Home in Crownsville
4.95 out of 5 average rating, 19 reviewsWelcome to Heron House! Annapolis Waterfront Oasis
Quick stats about holiday rentals in Annapolis
Total rentals
670 properties
Total number of reviews
33K reviews
Family-friendly rentals
460 properties are a good fit for families
Pet-friendly rentals
200 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
370 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Outer Banks Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a fireplace Annapolis
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- Flat rentals Annapolis
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- Rentals with an EV charger Annapolis
- Rentals with a patio Annapolis
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- Rentals with a firepit Annapolis
- Rentals with a hot tub Annapolis
- Private suite rentals Annapolis
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- Rentals with pools Annapolis
- Fitness-friendly rentals Annapolis
- Family-friendly rentals Annapolis
- Nationals Park
- The White House
- National Mall
- Georgetown University
- District Wharf
- Oriole Park at Camden Yards
- Betterton Beach
- Smithsonian National Museum of Natural History
- M&T Bank Stadium
- National Museum of African American History and Culture
- Sandy Point State Park
- Hampden
- Arlington National Cemetery
- Patterson Park
- Caves Valley Golf Club
- Georgetown Waterfront Park
- Six Flags America
- Washington Monument
- Great Falls Park
- Crystal Beach Manor, Earleville, MD
- National Harbor
- Smithsonian American Art Museum
- Library of Congress
- Lincoln Park