Sailing Yacht Charter Chesapeake Bay Sailboat Charters & Rentals

13 Sailboats and Sailing Yachts in Chesapeake Bay available - Bareboat Sailing Charters, Sailing Yacht Rentals with Crew and Captain or Skippered Sailing Boat Charters - Rent a Sailing Boat in Chesapeake Bay ONLINE! Sailing Vacation United States of America
Filter summary: Location Chesapeake Bay boat type Sailing boat

Available yacht charter boats in Chesapeake Bay within the next six months:

  • Sailing yacht Hunter 33 for charter in Port Annapolis Marina

    Sailing yacht Hunter 33 for charter in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2009 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 1 passenger
    • Hunter 33[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 2.716 per week
    from $ 3,243 per week
    View Details
  • Sail boat Dufour 382 Grand Large for rent in Annapolis

    Sail boat Dufour 382 Grand Large for rent in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2017 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 1 passenger
    • Dufour 382 Grand Large[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 4.179 per week
    from $ 4,990 per week
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  • Sailing boat Jeanneau 53 available for charter in Annapolis

    Sailing boat Jeanneau 53 available for charter in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2011 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 1 passenger
    • Jeanneau 53[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 5.195 per week
    from $ 6,204 per week
    View Details
  • Sail boat Sun Odyssey 45DS for charter in Port Annapolis Marina

    Sail boat Sun Odyssey 45DS for charter in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2008 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 1 passenger
    • Sun Odyssey 45DS[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 4.130 per week
    from $ 4,932 per week
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  • Sail boat Sun Odyssey 409 for hire in Annapolis

    Sail boat Sun Odyssey 409 for hire in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2012 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 1 passenger
    • Sun Odyssey 409[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 4.025 per week
    from $ 4,806 per week
    View Details
  • Sailing yacht Dufour 460 Grand Large for rent in Port Annapolis Marina

    Sailing yacht Dufour 460 Grand Large for rent in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2017 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 1 passenger
    • Dufour 460 Grand Large[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Best Price Instant Confirmation
    from 5.163 per week
    from $ 6,166 per week
    View Details
  • Yacht Sun Odyssey 409 for rent in Annapolis

    Yacht Sun Odyssey 409 for rent in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2013 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 1 passenger
    • Sun Odyssey 409[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 3.678 per week
    from $ 4,395 per week
    View Details
  • Sailing yacht Sun Odyssey 409 available for charter in Port Annapolis Marina

    Sailing yacht Sun Odyssey 409 available for charter in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2012 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 1 passenger
    • Sun Odyssey 409[Yacht Price incl. Taxes]
    • Cockpit cushion
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 3.917 per week
    from $ 4,680 per week
    View Details
  • Yacht Oceanis 34 for rent in Port Annapolis Marina

    Yacht Oceanis 34 for rent in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2011 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 1 passenger
    • Oceanis 34[Yacht Price incl. Taxes]
    • Barbeque Grill
    • Cockpit cushion
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 3.164 per week
    from $ 3,778 per week
    View Details
  • Sailing yacht Sun Odyssey 50DS available for charter in Annapolis

    Sailing yacht Sun Odyssey 50DS available for charter in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2011 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 1 passenger
    • Sun Odyssey 50DS[Yacht Price incl. Taxes]
    • Barbeque Grill
    • Cockpit cushion
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 4.980 per week
    from $ 5,950 per week
    View Details
  • Sail boat Sun Odyssey 469 for charter in Annapolis

    Sail boat Sun Odyssey 469 for charter in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2014 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 1 passenger
    • Sun Odyssey 469[Yacht Price incl. Taxes]
    • Barbeque Grill
    • Cockpit cushion
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 4.512 per week
    from $ 5,392 per week
    View Details
  • Sailing yacht Oceanis 45 available for charter in Port Annapolis Marina

    Sailing yacht Oceanis 45 available for charter in Port Annapolis Marina

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2013 - Cabins: 3 - Berths: 6
    Bareboat charter
    Max 6 persons
    The price is calculated for 7 day charter and 1 passenger
    • Oceanis 45[Yacht Price incl. Taxes]
    • Cockpit cushion
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 4.615 per week
    from $ 5,511 per week
    View Details
  • Sailing yacht Sun Odyssey 44 DS for rent in Annapolis

    Sailing yacht Sun Odyssey 44 DS for rent in Annapolis

    Sailing boat Rentals Chesapeake Bay › Annapolis (Maryland)
    Sailing boat - Built in: 2013 - Cabins: 2 - Berths: 4
    Bareboat charter
    Max 4 persons
    The price is calculated for 7 day charter and 1 passenger
    • Sun Odyssey 44 DS[Yacht Price incl. Taxes]
    • Yacht Insurance
    • Final cleaning
    • Damage waiver
    • Bed linen
    • Service fee
    • Boat preparation
    • Maryland Amusement Tax
    • VAT or sales tax
    Confirmed in 24h
    from 4.296 per week
    from $ 5,133 per week
    View Details
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This yacht is available with skipper/crew only.You are able to charter and drive this boat yourself. A skipper can be booked as an additional extra if required.The maximum number of guests this boat can accommodate.