Annapolis, MD, US holiday homes: holiday houses & more

Discover a selection of 446 holiday homes in Annapolis, MD, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Bookabach holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at NZ$ 180 per night, and holiday houses and cottages are popular options for a stay in Annapolis. Either way, you'll find accommodation for everyone's needs.

DynamicDestinationRefinements

AsyncDestinationUrgency

Find the best place to stay — Annapolis

Search 446 holiday rentals

Stayed Oct 2021

Perfect location for USNA Reunion

This house is fantastic and we loved our stay! Perfect for a USNA reunion weekend, and what a huge perk the parking pass was - we parked once and walked everywhere. We’ve stayed at multiple hotels in Annapolis over the last 20 years and this house be...

Stayed Oct 2021

Girls Trip

We went to Annapolis for all girls (5) weekend for my SIL’s 40th birthday. Stayed at 421 for three nights. We really enjoyed our stay, Liz is very friendly, welcoming and approachable. The house is cozy and clean, weren’t able to utilize the pool due...

Stayed Oct 2021

Fantastic place for our weekend trip to Annapolis!!! Beth & Andy were super nice and helpful!!!

Perfect place for our weekend trip to Annapolis!! The little extras made such nice place even better. Keurig with all the fixings, waters and snacks, Etc. Etc. The pool was perfect for us!!!! Bed and linens were comfy and clean. Super open layout wit...

Stayed Oct 2021

Amazing property!

The location, property, and owners are all amazing. My husband and our 3 kids stayed here for 3 nights and had the best time. It is a great location to anywhere you want to go. The owners are fantastic and even brought us ponchos and umbrellas when a...

Stayed Oct 2021

Annapolis Boat Show Stay

We travelled to Annapolis from California to attend the Annapolis Boat Show for the first time ever! The show was fantastic and we loved Annapolis. We also loved Joie's home away from home. She called me the morning of our trip to touch base and see ...

Stayed Oct 2021

Cute cottage, a perfect tiny home away from home for young couples

My family enjoyed the beautiful grounds and picturesque views. The cottage itself has a tiny house feel that is absolutely perfect for young/middle aged couples (the ladder into the loft requires some dexterity, seniors or the physically challenged m...

Stayed Oct 2021

Simply Amazing.

This place was extremely well put together. The owners were outstanding. The kitchen was awesome for anyone looking for a family gathering. The location couldn’t be beat. A block from the boat show, Main Street and a nice park for kids in the other d...

Stayed Oct 2021

Perfect for a visit to Annapolis

Miller's cottage is in a convenient location for your visit to the Annapolis area. Owners are great and very accommodating. Cottage is comfortable and well equipped. We visited during a busy weekend in Annapolis. Traffic/parking downtown was difficul...

AsyncDestinationInfographic

AsyncExploreBookEnjoy

How many holiday homes are available around Annapolis, MD, US?

Our 2021 holiday accommodation listings offer a large selection of 446 holiday rentals around Annapolis. From 355 holiday houses to 20 cottages, find unique holiday house for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Annapolis is on Bookabach.

What is the best area to stay when travelling to Annapolis?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Annapolis:

Epping Forest: 18 holiday homes
Historic District: 105 holiday homes
Homewood: 48 holiday homes
Hillsmere: 18 holiday homes
Eastport: 135 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Annapolis?

Bookabach.co.nz offers a large selection of holiday accommodations near great places in Annapolis. From Bookabach.co.nz travellers, the most popular points of interest to stay near are:

Hammond-Harwood House: 586 holiday houses
Asbury United Methodist Church: 583 holiday houses
Jonas Green State Park: 563 holiday houses
The Kunta Kinte Alex Haley Memorial: 559 holiday houses
Maryland Quiet Waters Park: 593 holiday houses

But there are many other points of interest around Annapolis listed on Bookabach.co.nz where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Annapolis?

Yes, of course. Bookabach.co.nz offers 355 Houses in Annapolis. Our other popular types of Annapolis holiday rentals include:

Cottages: 20 self catering accommodations
Condos/Apartments: 77 self catering accommodations
Cabins: 21 self catering accommodations

But you can also enjoy a great stay in one of our other holiday homes including Boats and more.

Can I find a holiday accommodation with pool in Annapolis?

Yes, you can select your preferred holiday accommodation with pool among our 73 holiday homes with pool available in Annapolis. Please use our search bar to access the selection of holiday rentals available.