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

Just Minutes from Black River – With WIFI

The Sutton House 2 blocks from Main Street & Courthouse Square

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

Charming 1860s Renovated Home

Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

Newly remodeled offers many amenities with perfect location!

Sunshine Shack at Clearwater Lake (sleeps 6)

Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

Spacious & Secluded Shook Home w/ Private Hot Tub!

Charming Country Bungalow - perfect for families

Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins
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 | 23 Holiday Homes |
---|---|
Lowest Price | NZ$316 |
Highest Price | NZ$850 |
Popular accommodation | Just Minutes from Black River – With WIFI, The Sutton House 2 blocks from Main Street & Courthouse Square, Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE, Charming 1860s Renovated Home, Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge, Newly remodeled offers many amenities with perfect location!, Sunshine Shack at Clearwater Lake (sleeps 6), Gorgeous large rental home in Lesterville MO just minutes from Blackwater River., Spacious & Secluded Shook Home w/ Private Hot Tub!, Charming Country Bungalow - perfect for families, Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins, Secluded Gate House |
More accommodations in Annapolis
Top trending hotels in Annapolis

Rustic River Cabin Getaway
^Eligibility requirements and conditions apply