Holiday rentals in Annapolis
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Top-rated holiday rentals in Annapolis
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Guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore.
Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged
Parties are not permitted.
Please note that there is no water access on the property, but there is nearby public water access.
14–21 FebIndividual Host,
£187 per night
4.96 out of 5 average rating, 326 reviews
Guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill & fire bowl. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.
25 Mar – 1 AprIndividual Host,
£810 per night
5.0 out of 5 average rating, 103 reviews
Guest favourite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!
24–31 JulIndividual Host,
£160 per night
4.94 out of 5 average rating, 305 reviews
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Quick stats about holiday rentals in Annapolis
Total rentals | 650 properties |
---|---|
Rentals with dedicated workspaces | 340 properties have a dedicated workspace |
Rentals with a pool | 40 properties have a pool |
Pet-friendly rentals | 180 properties allow pets |
Family-friendly rentals | 450 properties are a good fit for families |
Total number of reviews | 28K reviews |
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