86+ Vacation Rentals Near Annapolis Sailing School |
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Old Mansions - Vacation Rentals in Annapolis Sailing School

Property Image From $538
         

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10.0 (6 Reviews)
House
Anchors Away Abode
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Property Image From $386
         

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9.6 (21 Reviews)
Bed & Breakfast
Inn at Horn Point
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Property Image From $365
         

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10.0 (5 Reviews)
House
Vintage Charm: Annapolis Retreat
  • Air Conditioner
  • Parking
  • View

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Property Image From $234
         

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9.4 (78 Reviews)
Bed & Breakfast
Flag House Inn
  • Air Conditioner
  • Parking
  • TV

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Property Image From $955
         

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10.0 (2 Reviews)
House
Oasis by the Bay - Waterfront Heated Pool Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $408
         

10.0 (2 Reviews)
Hotel
86 State Circle - Luxury Boutique Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

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Property Image From $320
         

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10.0 (2 Reviews)
House
Skyline Sanctuary
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

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Property Image From $378
         

9.8 (28 Reviews)
Hotel
134 Prince - Luxury Boutique Hotel
  • Air Conditioner
  • Parking
  • TV

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Property Image From $263
         

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10.0 (2 Reviews)
Apartment
USNA Home In Downtown Annapolis
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $177
         

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9.4 (1014 Reviews)
Hotel
Graduate by Hilton Annapolis
  • Air Conditioner
  • Parking
  • TV

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Property Image From $1,065
         

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10.0 (1 Review)
House
Harrison Hall
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

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Property Image From $166
         

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9.0 (1869 Reviews)
Hotel
Historic Inns of Annapolis
  • Air Conditioner
  • Parking
  • TV

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Property Image From $727
         

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10.0 (1 Review)
House
Anchors Aweigh
  • Air Conditioner
  • Security/Safety
  • Sports/Activities

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Property Image From $154
         

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9.0 (153 Reviews)
Hotel
Fairfield Inn & Suites By Marriott Annapolis
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

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Property Image From $426
         

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10.0 (1 Review)
House
All Star Annapolis Retreat - Walk To Stadium
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $232
         

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8.8 (871 Reviews)
Hotel
Annapolis Waterfront Hotel, Autograph Collection
  • Air Conditioner
  • Parking
  • TV

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Property Image From $304
         

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10.0 (1 Review)
House
* Midcentury Modern Getaway * Prime Location *
  • Air Conditioner
  • Parking
  • View

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Property Image From $251
         

9.9 (8 Reviews)
House
Weems Creek Cottage, Annapolis Waterfront
  • Air Conditioner
  • Parking
  • Security/Safety

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Property Image From $203
         

9.7 (7 Reviews)
Apartment
BayRidge house by Quiet Waters, Thomas Point Parks
  • Air Conditioner
  • Parking
  • Security/Safety

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Property Image From $467
         

9.6 (6 Reviews)
House
Private Single Family Home Close to Both Water and Downtown!
  • Air Conditioner
  • Parking
  • View

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Property Image From $225
         

9.4 (9 Reviews)
Apartment
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Property Image From $244
         

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9.3 (12 Reviews)
Apartment
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating

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Property Image From $359
         

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9.1 (8 Reviews)
House
Walk to Everything Historic Arts District
  • Air Conditioner
  • Parking
  • Security/Safety

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Property Image From $440
         

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9.1 (6 Reviews)
House
Fisher House - Downtown Annapolis!
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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★ Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Annapolis Sailing School.

Weather in Annapolis Sailing School

View the weather forecast for Annapolis Sailing School before booking your Annapolis Sailing School Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Annapolis Sailing School, MD

Old Mansions offers a large selection of top attractions around Annapolis Sailing School. Research things to do on your vacation before you visit Annapolis Sailing School.


U.S. Naval Academy Westfield Annapolis Mall Annapolis City Dock Chesapeake Bay Bridge Sandy Point State Park Anne Arundel Medical Center Maryland State House Navy-Marine Corps Memorial Stadium Annapolis Harbour Center Kunta Kinte–Alex Haley Memorial Annapolis Maritime Museum Maryland Quiet Waters Park St John's College Bay Hills Golf Club Maryland World War II Memorial William Paca House Renditions Golf Club The Kunta Kinte Alex Haley Memorial Maryland Hall for Creative Arts Thurgood Marshall Memorial