Holiday rentals near Annapolis Sailing School
We found 1,136 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 Jul - 10 Jul
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 NZ$15,457
NZ$15,457
for 7 nights, 1 home
NZ$2,208 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 NZ$959
NZ$959
for 7 nights, 1 home
NZ$137 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 NZ$8,470
NZ$8,470
for 7 nights, 1 home
NZ$1,210 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
7% off
Price is NZ$13,744
NZ$13,744
for 7 nights, 1 home
NZ$1,963 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 NZ$7,438
NZ$7,438
for 7 nights, 1 home
NZ$1,063 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 NZ$6,020
NZ$6,020
for 7 nights, 1 apartment
NZ$860 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 NZ$3,982
NZ$3,982
for 7 nights, 1 home
NZ$569 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, (22 reviews)
Exceptional
(22 reviews)
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Annapolis
12% off
Price is NZ$4,113
NZ$4,113
for 7 nights, 1 room
NZ$588 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 NZ$10,951
NZ$10,951
for 7 nights, 1 home
NZ$1,564 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
7% off
Price is NZ$7,311
NZ$7,311
for 7 nights, 1 home
NZ$1,044 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
8% off
Price is NZ$3,016
NZ$3,016
for 7 nights, 1 apartment
NZ$431 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 NZ$6,685
NZ$6,685
for 7 nights, 1 home
NZ$955 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 NZ$11,513
NZ$11,513
for 7 nights, 1 home
NZ$1,645 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 NZ$8,307
NZ$8,307
for 7 nights, 1 cottage
NZ$1,187 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 NZ$2,547
NZ$2,547
for 7 nights, 1 apartment
NZ$364 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 NZ$6,956
NZ$6,956
for 7 nights, 1 home
NZ$994 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 NZ$10,735
NZ$10,735
for 7 nights, 1 home
NZ$1,534 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 NZ$3,314
NZ$3,314
for 7 nights, 1 cottage
NZ$473 per night
includes taxes & fees
Image gallery for Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
St. Michaels
17% off
Price is NZ$7,809
NZ$7,809
for 7 nights, 1 home
NZ$1,116 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 NZ$3,626
NZ$3,626
for 7 nights, 1 cottage
NZ$518 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 NZ$3,373
NZ$3,373
for 7 nights, 1 home
NZ$482 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 NZ$2,955
NZ$2,955
for 7 nights, 1 apartment
NZ$422 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 NZ$2,083
NZ$2,083
for 7 nights, 1 cottage
NZ$298 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 NZ$7,245
NZ$7,245
for 7 nights, 1 home
NZ$1,035 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
54 reviews
(54 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
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