Annapolis house rentals
We found 560 house rentals — enter your dates for availability
Explore Annapolis house rentals
Stunning Waterfront Cottage in the Sailing Capital of the World!
Sleeps 6 · 2 bedrooms · 1 bathroom
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Sleeps 8 · 3 bedrooms · 1+ bathroom
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Sleeps 18 · 6 bedrooms · 4 bathrooms
Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
Sleeps 4 · 1 bathroom
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
Fabulous 5-bedroom house with AC in charming Annapolis
Sleeps 10 · 5 bedrooms · 2 bathrooms
Top rated house rentals - Annapolis
Lovely townhome in the heart of the historic district
19 Pinkney is a very charming, very comfortable and quiet townhome in the heart of the downtown historic district. From the time we walked in we felt like it was home while we enjoyed everything that Annapolis had to offer. The house was very well stocked! The location was perfect! The assigned parking space right outside the door was a bonus! It was so nice to park our car and walk throughout the charming little streets in the historic district admiring the beautiful historical buildings and homes that were all decorated for the holidays. We really appreciated being so close to all of the wonderful restaurants, pubs, galleries, shops and City Dock. Eastport with its fun, casual eateries was also just a few minutes away. The owner was very nice and very helpful answering any questions that we had. Her suggestions for restaurants were wonderful! We tried every one and added them to our usual list of favorites. We try to visit Annapolis at least once a year and would love to return to 19 Pinkney when we do.
Maureen S.
Stayed Dec 2017
Fantastic house - clean, warm & perfectly located to get around Annapolis
Property was fully equipped with everything we needed - like a ‘home away from home’. John was extremely helpful and informative during our planning and everything was as we expected. Thanks a lot!
Simon M.
Stayed Dec 2017
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Frequently asked questions
Are there any holiday home rentals in Annapolis?
Choose from 560 holiday home rentals in Annapolis that have more space, privacy, value and amenities compared to a hotel room. Browse houses in well-known areas such as Historic District, Naval Academy and Murray Hill.
How much does it cost to stay in a holiday rental house in Annapolis?
Your dream holiday home rental in Annapolis is waiting to be discovered, with prices varying from wallet-friendly stays to more high-end properties. Enter your travel details and then filter based on your preferences, making sure you find the right place for you and your favourite people.
When is the best time to rent a holiday house in Annapolis?
The majority of guests love to stay in a holiday home rental in Annapolis during the month of August. At this time of year, average temperatures range between 21ºC and 29ºC in this part of Central Maryland.
Where can I rent an Annapolis holiday house with great views?
Jump in and book one of our Annapolis houses with views of historic areas. The only thing better than spending your trip in a Stayz holiday home rental? Kicking back in a property with spectacular scenery just beyond your window.
Does Annapolis have any weekend house rentals?
Browse our weekend rentals and start packing for a fun-filled couple of days away. Our main tips for booking your ideal house in Annapolis? Be flexible when searching and modify your travel dates until you find the holiday home rental that fits your needs.
Are there any pet-friendly house rentals in Annapolis?
With 12 pet-friendly holiday home rentals in Annapolis, you can enjoy your next getaway with your furry friend right by your side. As well as comfortable beds for everyone, many houses also include perks like doggie bowls and free treats. Browse what's available by selecting the "Pets allowed" filter.
What are the top things to do in Annapolis?
Planning an unforgettable escape to Annapolis means finding awesome things that the family will enjoy. William Paca House, Chesapeake Bay Bridge and Sandy Point State Park are just two of the many options here. And Stayz's holiday home rentals are the ideal base for your sightseeing pursuits.
Why should I book my holiday rental house with Stayz?
Great customer support from the moment you book until after your trip is among several reasons to choose Stayz for your holiday home rental. We also offer properties that go beyond the basic hotel room — think houses in amazing locations, whether that's by the beach or along a lakeshore. And with flexible cancellation policies and benefits like payment protection, we offer peace of mind.