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

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

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Scenic Waterfront Getaway with Private Pool and Dock Minutes from 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!

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

Charming brick home with patio, WiFi, AC, & W/D - walk to everything

18th Cent. Charm in Historic Downtown Annapolis

Charming Historic Annapolis Home With Two Off-street Parking Places!

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

Timeless Charm Meets Modern Comfort

The Yellow Cottage on Harness Creek

Private Waterfront Woods | Dock, Kayaks, Views

7 mins away from Downtown Annapolis

Walk to the stadium! - Lighthouse on Glenwood

Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

Fabulous 5-bedroom house with AC in charming Annapolis

Luxury Pool Loft sleeps 4
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.
Top Holiday Rental Destinations
Top 20 Annapolis Hotels
More destinations for you
- Santa Barbara Accommodation
- Grovetown Accommodation
- Palm Springs Accommodation
- Groveland Accommodation
- Pullman Accommodation
- South Lake Tahoe Accommodation
- Lahaina Accommodation
- Anaheim Accommodation
- Cambridge Accommodation
- Hamilton Accommodation
- Catlin Accommodation
- Venice Accommodation
- Cumberland Accommodation
- Tall Timbers Accommodation
- Royal Oak Accommodation
- Pet Friendly Hotels in Oxford
- Sherwood Accommodation
- Christmas Accommodation
- St. Michaels Accommodation
- Honolulu Accommodation
- Monterey Accommodation
- Bayview Accommodation
- All Inclusive Hotels in Honolulu
- San Diego Accommodation
- Bel Air Accommodation
- Kailua-Kona Accommodation
^Eligibility requirements and conditions apply








