Annapolis Vacation Rentals

Compare 32 vacation rentals. Enter your trip dates to get started.
USA > Maryland > Annapolis

Make Annapolis your next getaway—choose from 32 great vacation rentals

Claim your spot in Maryland’s capital city with Annapolis vacation rentals. This seaside city offers a chance to admire historical architecture, tour maritime museums, and fill up on seafood. Discover something new along the east coast. 

Explore Annapolis house rentals, and more

housing_type_house.jpg

House rentals

View 32 House rentals

Annapolis vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
The King's Court
4 Bedroom | 3.5 Bath | Sleeps 8

The King's Court - Annapolis, MD

$767 avg / night
Waterside with it All
6 Bedroom | 6 Bath | Sleeps 18

Waterside with it All - Annapolis, MD

$1,202 avg / night
The Ship's Bridge
4 Bedroom | 3.5 Bath | Sleeps 10

The Ship's Bridge - Annapolis, MD

$934 avg / night
Anchors Aweigh
4 Bedroom | 2.5 Bath | Sleeps 8

Anchors Aweigh - Annapolis, MD

$942 avg / night
Ferry Point Pastures
4 Bedroom | 2.5 Bath | Sleeps 9

Ferry Point Pastures - Annapolis, MD

$692 avg / night

View 27 more homes

Recent Annapolis vacation rental reviews

Beautiful house well furnished and stocked (especially the kitchen).
Gwenn C. | Sep 2022
This large historic home is freshly remodeled with a perfect mix of style, luxury and comfort. It's made for entertaining with its oversized family room, kitchen and back patio deck. The enormous Master Suite comes equipped with motorized window shades, dual head walk-in shower and style galore. While it is well located in Eastport and it's charming streets, eateries and boating clubs, it is still only a 10-15 gorgeous stroll across the water to bustling downtown Annapolis and Gate 1 of the US Naval Academy. Harrison Hall easily rates as the best of many places we have stayed in Annapolis over the past few years.
Craig & Janelle F. | Sep 2022
This home is absolutely AMAZING! So beautiful, comfortable, and well stocked. The location is prime real estate and the fact that it comes with a parking spot puts it over the top. We rented for our mids 2nd class parents weekend and loved it. We were able to have our mid, his friends, and their parents over to finally meet and there was plenty of room. The outside patio is beautiful and large. You can cook for 20 people in the kitchen. The kitchen has every upgrade imaginable and anything you would need for cooking. They have all the seasoning, oils, condiments, etc...it was great! The bedrooms were very comfortable and well sized. We did not use the trundle bed on the 2nd floor, instead the kids slept on the 3rd floor. The third floor has 2 twins not bunk beds, but plenty of space to sleep more if the kids want to be together. This is probably our most favorite home that we have rented in our mid's 2 years at the Academy and I hope we can come back some day! Thank you for sharing your lovely home with a Utah family that loved being in Annapolis with their mid!
Julie P. | Sep 2022
Annapolis Frequently Asked Questions

Yes, 8 of our Annapolis homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 37 of our Annapolis vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Annapolis vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Annapolis team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Annapolis, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Explore our Annapolis, MD, vacation rentals

Take in the sights of Chesapeake Bay with Annapolis vacation rentals. Maryland’s capital city lies about 45 minutes from both Washington D.C. and Baltimore, making it the perfect home base for exploring the east coast. Spend your afternoons hopping from museum tour to farmers market, then wind down your evenings enjoying a stroll along the waterfront. 

Take a step through time at the William Paca House & Garden, reel in a catch at Sandy Point State Park, or enjoy a fresh crab dinner at one of the many mom-and-pop seafood restaurants dotting the coast. If you’re interested in daytripping, Baltimore’s harbor hosts historic warships and museums, and nearby D.C. famously boasts a number of national landmarks. Book your stay and start your adventure.