Holiday Rentals in Annapolis
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Holiday Rentals in Annapolis

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

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Beautiful Condo - Water View Near City Dock

7 mins away from Downtown Annapolis

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Your Annapolis Adventure Starts Here!!

Secluded Cozy Cottage in Historic Downtown

Annapolis Condominium in the heart of the historic center

Charming Annapolis WaterVIEW Home

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

Recently Renovated Annapolis Home - Conveniently Located

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

Historic Annapolis Home 1.5 blocks from center of town.

MODERN 2022 NEWLY BUILT TOWNHOME

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Other types of properties in Annapolis you may be interested in

Historic Inns of Annapolis
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.
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