Annapolis Holiday Homes
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
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Annapolis

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

Charming Annapolis WaterVIEW Home

Waterfront Home with Private Dock, Community Beach

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

Eastport Cottage .5 mi from Downtown Annapolis

Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis

Walkable to Main Street at Seashell in the City with 2 parking spots

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Parking at Randall House Across from USNA Gate 1

Charming, Newly Renovated Historic Row Home in Downtown Annapolis

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
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 | 284 Holiday Homes |
|---|---|
Lowest Price | NZ$192 |
Highest Price | NZ$1,434 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Charming Annapolis WaterVIEW Home, Waterfront Home with Private Dock, Community Beach, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Eastport Cottage .5 mi from Downtown Annapolis , Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis, Walkable to Main Street at Seashell in the City with 2 parking spots, Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, Parking at Randall House Across from USNA Gate 1, Charming, Newly Renovated Historic Row Home in Downtown Annapolis, Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! |
Top trending hotels in Annapolis

DoubleTree by Hilton Hotel Annapolis
^Eligibility requirements and conditions apply







