Historic District holiday homes
We found 189 holiday rentals — enter your dates for availability
Discover a selection of 156 homes, 20 apartments and other holiday rentals in Historic District that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include a garden and pool. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.
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Find the best place to stay - Historic District

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
Sleeps 5 · 2 bedrooms · 1+ bathroom
10 out of 10
exceptional
(159 reviews)

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Sleeps 8 · 3 bedrooms · 1+ bathroom
10 out of 10
exceptional
(224 reviews)

Freshly renovated 3-story home 1 block from USNA!
Sleeps 10 · 3 bedrooms · 2+ bathrooms
9.8 out of 10
exceptional
(34 reviews)

Secluded Cozy Cottage in Historic Downtown
Sleeps 8 · 2 bedrooms · 1 bathroom
9.4 out of 10
exceptional
(12 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value