Holiday rentals near Annapolis Harbor
We found 683 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals near Annapolis Harbor that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you expect for your stay, which might include parking and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Annapolis Harbor
Showing deals for:19 Dec - 26 Dec
Image gallery for Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Stevensville, MD
8% off
Price is AU$7,659
for 7 nights, 1 cottage
AU$1,094 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Annapolis Harbor
Governor Calvert Suite at Historic Inns of Annapolis
Sleeps 4 · 1 bedroom · 1 bathroom
Top rated rentals - Annapolis Harbor
SPECTACULAR!!!
10 out of 10
exceptional
(197 reviews)
CONGRATULATIONS! You have found the best house on Kent Island and all of VRBO.We just finished an incredible stay here and were blown away from the moment we pulled up the driveway. The house is spotless, beautifully decorated, and fully stocked with everything you could possibly need. The amenities truly went above and beyond. The outdoor spaces are immaculate and luxurious, with a wraparound porch on both levels and a breathtaking pool. Our family especially enjoyed the daily deer sightings on the property.As for the host, John was extremely hospitable. His attention to detail is unmatched. He was accessible, accommodating, and made sure everything was perfect for our stay.We will forever cherish the family memories we made here. If you're lucky enough to see this place available, book it!
Charlene U.
Stayed June 2025
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