Holiday rentals near Annapolis Sailing School
We found 1,174 holiday rentals — enter your dates for availability
Choose the perfect private holiday rental within close proximity to Annapolis Sailing School. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Annapolis Sailing School
Showing deals for:2 Jan - 9 Jan
Image gallery for One-level waterfront home with beach and stunning views all the way to the Bay Bridge
9.8 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
One-level waterfront home with beach and stunning views all the way to the Bay Bridge
Stevensville, MD
5% off
Price is AU$4,920
for 7 nights, 1 home
AU$703 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Annapolis Sailing School
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Sleeps 18 · 6 bedrooms · 4 bathrooms
10 out of 10
exceptional
(36 reviews)
Top rated rentals - Annapolis Sailing School
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