Annapolis Holiday Homes
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Featured Holiday Homes in Annapolis

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

PERFECT LOCATION in the heart of history

Charming townhome with AC and WiFi in delightful Annapolis

Private Cottage on gated estate

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Holiday Accommodation Annapolis
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Annapolis are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Annapolis itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Annapolis holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Annapolis, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Annapolis with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Annapolis Holiday Homes essential information
Accommodation | 342 Holiday Homes |
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Highest Price | |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium, Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything, PERFECT LOCATION in the heart of history, Charming townhome with AC and WiFi in delightful Annapolis, Private Cottage on gated estate, NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St., Wright's Cottage- Pet's Welcome & EV Charging, Recently Renovated Annapolis Home - Conveniently Located |
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Historic Inns of Annapolis
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