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:2 Oct - 9 Oct
Image gallery for House near Patapsco River 2700 square feet
9.49.4 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
House near Patapsco River 2700 square feet
Pasadena
8% off
Price is AU$7,891
AU$7,891
for 7 nights, 1 home
AU$1,127 per night
includes taxes & fees
Image gallery for Waterfront Home near Annapolis, MD
1010 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Waterfront Home near Annapolis, MD
Galesville
8% off
Price is AU$19,496
AU$19,496
for 7 nights, 1 home
AU$2,785 per night
includes taxes & fees
Image gallery for Waterfront Architectural Masterpiece with private dockage available.
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Waterfront Architectural Masterpiece with private dockage available.
Annapolis
7% off
Price is AU$14,712
AU$14,712
for 7 nights, 1 home
AU$2,102 per night
includes taxes & fees
Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!
9.89.8 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Captain's Retreat! Newly Renovated - few steps from the beach!
Annapolis
16% off
Price is AU$8,344
AU$8,344
for 7 nights, 1 home
AU$1,192 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$6,133
AU$6,133
for 7 nights, 1 home
AU$876 per night
includes taxes & fees
Image gallery for Love Point Waterfront Home....Chesapeake Bay views....Pets OK
9.49.4 out of 10, Exceptional, (123 reviews)
Exceptional
(123 reviews)
Love Point Waterfront Home....Chesapeake Bay views....Pets OK
Stevensville
8% off
Price is AU$5,110
AU$5,110
for 7 nights, 1 home
AU$730 per night
includes taxes & fees
Image gallery for Mins to Annap; Luxury Townhome
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Mins to Annap; Luxury Townhome
Arnold
8% off
Price is AU$7,464
AU$7,464
for 7 nights, 1 home
AU$1,066 per night
includes taxes & fees
Image gallery for Waterfront 4 BR home with private pier and boat dock
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Waterfront 4 BR home with private pier and boat dock
Grasonville
8% off
Price is AU$7,577
AU$7,577
for 7 nights, 1 home
AU$1,082 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$3,292
AU$3,292
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Image gallery for Circa 1700 Chesapeake Colonial home on the National Register.
9.89.8 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville
8% off
Price is AU$5,615
AU$5,615
for 7 nights, 1 home
AU$802 per night
includes taxes & fees
Image gallery for The General's House-Spacious Home w/Pool & Hot Tub
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
The General's House-Spacious Home w/Pool & Hot Tub
Annapolis
7% off
Price is AU$11,564
AU$11,564
for 7 nights, 1 home
AU$1,652 per night
includes taxes & fees
Image gallery for Waterfront Sanctuary only 50 Min. From DC/Balt.
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Waterfront Sanctuary only 50 Min. From DC/Balt.
Shady Side
12% off
Price is AU$8,081
AU$8,081
for 7 nights, 1 home
AU$1,154 per night
includes taxes & fees
Image gallery for Annapolis Tree House Apartment- luxury shower, separate space
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Annapolis Tree House Apartment- luxury shower, separate space
Annapolis
7% off
Price is AU$2,539
AU$2,539
for 7 nights, 1 apartment
AU$363 per night
includes taxes & fees
Image gallery for Edgewater's Shelby on the Bay
9.49.4 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Edgewater's Shelby on the Bay
Edgewater
7% off
Price is AU$6,564
AU$6,564
for 7 nights, 1 home
AU$938 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$4,748
AU$4,748
for 7 nights, 1 cottage
AU$678 per night
includes taxes & fees
Image gallery for Guest Quarters at the Inn - 102
9.89.8 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Guest Quarters at the Inn - 102
North Beach
8% off
Price is AU$2,123
AU$2,123
for 7 nights, 1 apartment
AU$303 per night
includes taxes & fees
Image gallery for The Liberty House- Pristine Renovation with parking,
1010 out of 10, Exceptional, (53 reviews)
Exceptional
(53 reviews)
The Liberty House- Pristine Renovation with parking,
Annapolis
8% off
Price is AU$6,020
AU$6,020
for 7 nights, 1 home
AU$860 per night
includes taxes & fees
Image gallery for Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Riva
8% off
Price is AU$5,941
AU$5,941
for 7 nights, 1 home
AU$849 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, (140 reviews)
Exceptional
(140 reviews)
Charming cottage along water with private pier, near St. Michaels Winery
Bozman
12% off
Price is AU$2,995
AU$2,995
for 7 nights, 1 cottage
AU$428 per night
includes taxes & fees
Image gallery for Heart of Historic District!
9.89.8 out of 10, Exceptional, (176 reviews)
Exceptional
(176 reviews)
Heart of Historic District!
Annapolis
26% off
Price is AU$4,671
AU$4,671
for 7 nights, 1 home
AU$667 per night
includes taxes & fees
Image gallery for Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
Riva
21% off
Price is AU$4,161
AU$4,161
for 7 nights, 1 home
AU$594 per night
includes taxes & fees
Image gallery for Cozy Cottage with Beach Access
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Cozy Cottage with Beach Access
Annapolis
7% off
Price is AU$4,465
AU$4,465
for 7 nights, 1 home
AU$638 per night
includes taxes & fees
Image gallery for Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
Annapolis
12% off
Price is AU$13,300
AU$13,300
for 7 nights, 1 home
AU$1,900 per night
includes taxes & fees
Image gallery for Water Views - Close to Downtown Annapolis
1010 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)
Water Views - Close to Downtown Annapolis
Annapolis
5% off
Price is AU$7,156
AU$7,156
for 7 nights, 1 home
AU$1,022 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Annapolis Sailing School
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Sleeps 12 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
210 reviews(210 reviews)
NEW! Charming Farm House in Historic Kent Island
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
16 reviews(16 reviews)
Annapolis waterfront "tiny house" in garden setting
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
261 reviews(261 reviews)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Sleeps 18 · 6 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Waterfront Unit | Dock, Kayaks & SUPs Included
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 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