Book Holiday Homes in Annapolis

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Featured Holiday Homes in Annapolis

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private Waterfront Woods | Dock, Kayaks, Views

Private Waterfront Woods | Dock, Kayaks, Views

Annapolis
Book a stay at this beach vacation home in Annapolis. Enjoy a beach locale, a garden, and patios. Popular attractions Annapolis Golf Club and Bay Ridge Beach ...
Private Waterfront Woods | Dock, Kayaks, Views
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Chase Lloyd House and Hammond-Harwood ...
Charming garden row home, easy 4 block walk to the heart of Annapolis.
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a garden, and patios. Popular attractions Navy-Marine Corps Memorial Stadium ...
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
La Maison - Stunning waterfront views with pool

La Maison - Stunning waterfront views with pool

Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, private pools, and a garden. Popular attractions Annapolis Harbour Center and ...
La Maison - Stunning waterfront views with pool
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Ellen O. Moyer Nature Park at Back ...
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Brand New Spacious Luxury Home

Brand New Spacious Luxury Home

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Spa Creek and Annapolis Landing Marina are ...
Brand New Spacious Luxury Home
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Annapolis
The price is NZ$918 per night from 12 Jan to 13 Jan
NZ$918
includes taxes & fees
12 Jan - 13 Jan 2025
Stay at this vacation home in Annapolis. Enjoy free WiFi, private pools, and breakfast (surcharge). Our guests praise the pool in our reviews. Popular attractions ...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Bay Hills Golf Club ...
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Annapolis Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Annapolis vacation homes are the perfect way for you to wing it.

Holiday houses in Annapolis let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Annapolis in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Annapolis adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Annapolis with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Annapolis vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Annapolis Holiday Homes essential information

Accommodation
276 Holiday Homes
Lowest Price
NZ$222
Highest Price
NZ$918
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Private Waterfront Woods | Dock, Kayaks, Views, Charming garden row home, easy 4 block walk to the heart of Annapolis., Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, La Maison - Stunning waterfront views with pool, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Brand New Spacious Luxury Home, 421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Top trending hotels in Annapolis

Crowne Plaza Annapolis, an IHG Hotel

Crowne Plaza Annapolis, an IHG Hotel

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is NZ$222 per night from 25 Dec to 26 Dec
NZ$222
includes taxes & fees
25 Dec - 26 Dec
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Crowne Plaza Annapolis, an IHG Hotel
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$276 per night from 30 Dec to 31 Dec
NZ$276
includes taxes & fees
30 Dec - 31 Dec
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
Graduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$369 per night from 26 Dec to 27 Dec
NZ$369
includes taxes & fees
26 Dec - 27 Dec
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
Historic Inns of Annapolis
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The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$341 per night from 23 Dec to 24 Dec
NZ$341
includes taxes & fees
23 Dec - 24 Dec
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
The Westin Annapolis
Don't see what you're looking for?
See all available properties in Annapolis
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.