Holiday rentals near Annapolis Sailing School
We found 1,132 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:3 July - 10 July
Image gallery for USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR
8.08.0 out of 10, Very good, (5 reviews)
Very good
(5 reviews)
USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR
Annapolis
16% off
Price is AU$12,826
AU$12,826
for 7 nights, 1 home
AU$1,832 per night
includes taxes & fees
Image gallery for Lower Level Loft - Adorable Studio Apt. Near BWI
9.49.4 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Lower Level Loft - Adorable Studio Apt. Near BWI
Millersville
8% off
Price is AU$790
AU$790
for 7 nights, 1 home
AU$113 per night
includes taxes & fees
Image gallery for Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Annapolis
12% off
Price is AU$7,134
AU$7,134
for 7 nights, 1 home
AU$1,019 per night
includes taxes & fees
Image gallery for Brand New Spacious Luxury Home
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Brand New Spacious Luxury Home
Annapolis
8% off
Price is AU$11,465
AU$11,465
for 7 nights, 1 home
AU$1,638 per night
includes taxes & fees
Image gallery for Charming Home located minutes from the Naval Academy and Downtown Annapolis
9.69.6 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Annapolis
8% off
Price is AU$6,173
AU$6,173
for 7 nights, 1 home
AU$882 per night
includes taxes & fees
Image gallery for Unbelievable beach views for 6
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Unbelievable beach views for 6
North Beach
8% off
Price is AU$4,669
AU$4,669
for 7 nights, 1 apartment
AU$667 per night
includes taxes & fees
Image gallery for Charming 3BDR Bungalow Near Annapolis
9.69.6 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Charming 3BDR Bungalow Near Annapolis
Riva
9% off
Price is AU$3,314
AU$3,314
for 7 nights, 1 home
AU$473 per night
includes taxes & fees
Image gallery for Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
9.89.8 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Annapolis
12% off
Price is AU$9,081
AU$9,081
for 7 nights, 1 home
AU$1,297 per night
includes taxes & fees
Image gallery for Mins to Annap; Luxury Townhome
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Mins to Annap; Luxury Townhome
Arnold
8% off
Price is AU$6,260
AU$6,260
for 7 nights, 1 home
AU$894 per night
includes taxes & fees
Image gallery for West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Annapolis
12% off
Price is AU$3,412
AU$3,412
for 7 nights, 1 room
AU$487 per night
includes taxes & fees
Image gallery for Annapolis Tree House Apartment- luxury shower, separate space
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Annapolis Tree House Apartment- luxury shower, separate space
Annapolis
7% off
Price is AU$2,557
AU$2,557
for 7 nights, 1 apartment
AU$365 per night
includes taxes & fees
Image gallery for Charming Waterfront Cottage Retreat near St. Michaels
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Charming Waterfront Cottage Retreat near St. Michaels
Bozman
12% off
Price is AU$7,061
AU$7,061
for 7 nights, 1 cottage
AU$1,009 per night
includes taxes & fees
Image gallery for Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
9.49.4 out of 10, Exceptional, (90 reviews)
Exceptional
(90 reviews)
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Pasadena
8% off
Price is AU$5,546
AU$5,546
for 7 nights, 1 home
AU$792 per night
includes taxes & fees
Image gallery for Guest Quarters at the Inn - 102
9.69.6 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Guest Quarters at the Inn - 102
North Beach
8% off
Price is AU$2,159
AU$2,159
for 7 nights, 1 apartment
AU$308 per night
includes taxes & fees
Image gallery for Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
9.89.8 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Stevensville
8% off
Price is AU$9,536
AU$9,536
for 7 nights, 1 home
AU$1,362 per night
includes taxes & fees
Image gallery for Beautiful Retreat Located in Rock Hall - walk to everything!
1010 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Beautiful Retreat Located in Rock Hall - walk to everything!
Rock Hall
14% off
Price is AU$5,770
AU$5,770
for 7 nights, 1 home
AU$824 per night
includes taxes & fees
Image gallery for Charming Annapolis Victorian
1010 out of 10, Exceptional, (73 reviews)
Exceptional
(73 reviews)
Charming Annapolis Victorian
Annapolis
8% off
Price is AU$8,904
AU$8,904
for 7 nights, 1 home
AU$1,272 per night
includes taxes & fees
Image gallery for Cute waterfront apartment -- 8 min from the beach!
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Cute waterfront apartment -- 8 min from the beach!
Rock Hall
8% off
Price is AU$2,502
AU$2,502
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
Image gallery for Perfect Waterview Cottage - St. Michaels Getaway
9.89.8 out of 10, Exceptional, (119 reviews)
Exceptional
(119 reviews)
Perfect Waterview Cottage - St. Michaels Getaway
Wittman
8% off
Price is AU$2,769
AU$2,769
for 7 nights, 1 cottage
AU$396 per night
includes taxes & fees
Image gallery for Brand New Cottage Steps from the Beach!
1010 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Brand New Cottage Steps from the Beach!
Rock Hall
8% off
Price is AU$2,817
AU$2,817
for 7 nights, 1 home
AU$402 per night
includes taxes & fees
Image gallery for Charming cottage along water with private pier, near St. Michaels Winery
9.69.6 out of 10, Exceptional, (137 reviews)
Exceptional
(137 reviews)
Charming cottage along water with private pier, near St. Michaels Winery
Bozman
12% off
Price is AU$3,015
AU$3,015
for 7 nights, 1 cottage
AU$431 per night
includes taxes & fees
Image gallery for Annapolis waterfront "tiny house" in garden setting
1010 out of 10, Exceptional, (247 reviews)
Exceptional
(247 reviews)
Annapolis waterfront "tiny house" in garden setting
Annapolis
8% off
Price is AU$1,770
AU$1,770
for 7 nights, 1 cottage
AU$253 per night
includes taxes & fees
Image gallery for Historic Annapolis Charmer <1Mile to NMC Stadium
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Historic Annapolis Charmer <1Mile to NMC Stadium
Annapolis
16% off
Price is AU$14,003
AU$14,003
for 7 nights, 1 home
AU$2,000 per night
includes taxes & fees
Image gallery for The Liberty House- Pristine Renovation with parking
1010 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
The Liberty House- Pristine Renovation with parking
Annapolis
8% off
Price is AU$6,015
AU$6,015
for 7 nights, 1 home
AU$859 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Annapolis Sailing School
Private Cottage on gated estate
Sleeps 5 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptional
exceptional
32 reviews
(32 reviews)
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptional
exceptional
53 reviews
(53 reviews)
Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting
Sleeps 7 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptional
exceptional
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Sleeps 6 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellent
excellent
3 reviews
(3 reviews)
Waterfront Oasis of Annapolis Star
Sleeps 4 · 1 bedroom
1010 out of 10
Exceptional
exceptional
81 reviews
(81 reviews)
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Sleeps 3 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptional
exceptional
87 reviews
(87 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