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Featured Holiday Homes in Tracys Landing

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
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

Shady Side
When you stay at this vacation home in Shady Side, you'll be near the beach and 5 minutes by car from Franklin Point State Park.
Calloway Drive Retreat | House in Shady Side
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Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Dollhouse in Central Historic St Michaels
Private Waterfront Woods | Dock, Kayaks, Views

Private Waterfront Woods | Dock, Kayaks, Views

Annapolis
With a stay at this vacation home in Annapolis, you'll be on the beach, within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
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
With a stay at this vacation home in Annapolis (Historic District), you'll be within a 5-minute walk of U.S. Naval Academy and Chase Lloyd House.
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

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

Annapolis
With a stay at this vacation home in Annapolis (Admiral Heights), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial ...
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and 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
With a stay at this vacation home in Annapolis, you'll be within a 5-minute drive of U.S. Naval Academy and Spa Creek.
Brand New Spacious Luxury Home
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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.

Tracys Landing 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 Tracys Landing vacation homes are the perfect way for you to wing it.

Holiday houses in Tracys Landing 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 Tracys Landing 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 Tracys Landing adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Tracys Landing 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 Tracys Landing 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.

Tracys Landing Holiday Homes essential information

Accommodation
492 Holiday Homes
Lowest Price
AU$154
Highest Price
AU$334
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Calloway Drive Retreat | House in Shady Side, Dollhouse in Central Historic St Michaels, 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, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Brand New Spacious Luxury Home

Top trending hotels in Tracys Landing

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

2.5 out of 5
55 Hampton Park Blvd, Capitol Heights, MD
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 2 Jan to 3 Jan
AU$154
includes taxes & fees
2 Jan - 3 Jan 2025
Located in Capitol Heights, La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway is connected to a shopping center, a 3-minute drive from FedEx Field and ...
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
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 AU$208 per night from 13 Jan to 14 Jan
AU$208
includes taxes & fees
13 Jan - 14 Jan 2025
Located in Annapolis, Crowne Plaza Annapolis, an IHG Hotel is a 3-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical ...
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 AU$252 per night from 30 Dec to 31 Dec
AU$252
includes taxes & fees
30 Dec - 31 Dec
With a stay at Graduate by Hilton Annapolis, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights ...
Graduate by Hilton Annapolis
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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 AU$334 per night from 26 Dec to 27 Dec
AU$334
includes taxes & fees
26 Dec - 27 Dec
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Historic Inns of Annapolis
Don't see what you're looking for?
See all available properties in Tracys Landing
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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.

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^Subject to availability and chosen travel dates.