Holiday Rentals in Annapolis
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Holiday Rentals in Annapolis

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

Waterfront Oasis of Annapolis Star

Luxury Waterfront Executive Family Home Annapolis with All Amenities

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

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

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Charming Historic Townhouse Steps From USNA

Cozy 2br home w/ parking in downtown Annapolis

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

Beautiful 2-bedroom water view house in Annapolis

The Yellow Cottage on Harness Creek

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

Recently Renovated Annapolis Home - Conveniently Located

Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

Pristine Downtown 1-Bedroom Steps from State House

USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
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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Top 20 Annapolis Hotels
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^Eligibility requirements and conditions apply