Holiday Rentals in Annapolis
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Check rental availability in Annapolis
Holiday Rentals in Annapolis
Charming Annapolis WaterVIEW Home
Firefly Cottage at the Cape, Hot Tub, Community beach enjoy summer USNA visits.
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Waterfront Oasis of Annapolis Star
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Prime Eastport Location - Waterfront Condo with Parking
The Yellow Cottage on Harness Creek
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Waterfront Home with Private Dock, Community Beach
Fabulous 5-bedroom house with AC in charming Annapolis
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Walkable to Main Street at Seashell in the City with 2 parking spots
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis
Beautiful Condo - Water View Near City Dock
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.
