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Chesapeake Bay, US Boat Rentals & Yacht Charters

Page 3 of 10231 listings

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
$285 HR | 10 Guests | Sea Ray Boat
Events in Washington · 10 guests

$285 HR | 10 Guests | Sea Ray Boat

5.0
Superowner
$285/hour
$350hr|11 Guests | Water Toys
Events in Washington · 11 guests

$350hr|11 Guests | Water Toys

5.0
Superowner
$350/hour
Your Aquatic Escape: Bayliner 180 | Fast, Fun & Ready to Cruise!
Powerboats in Arlington · 6 guests

Your Aquatic Escape: Bayliner 180 | Fast, Fun & Ready to Cruise!

5.0
$100+/hour
Private Yacht Charter: On 40ft Regal Commodore
Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0
$400/hour
Limited Availability
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Powerboats in Annapolis · 8 guests

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

4.9
$225/hour
Sanpan 2500 RE Pontoon in Washington, Living room comfort on the water!
Powerboats in Washington · 10 guests

Sanpan 2500 RE Pontoon in Washington, Living room comfort on the water!

5.0
$200/hour
Limited Availability
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
2024 Luxury Avalon Pontoon 25' Quad Lounger, Spacious & Premium Experience
Powerboats in Washington · 12 guests

2024 Luxury Avalon Pontoon 25' Quad Lounger, Spacious & Premium Experience

5.0
$185/hour
Limited Availability
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

4.9
Superowner
$117+/hour
$250 hr | 6 Guests | Small Boat
Powerboats in Washington · 8 guests

$250 hr | 6 Guests | Small Boat

5.0
Superowner
$250/hour
$150hr |6 Guests | Bayliner Small boat
Events in Washington · 6 guests

$150hr |6 Guests | Bayliner Small boat

5.0
Superowner
$175/hour
Limited Availability
41' Meridian Sedan Yacht for Charter in Washington, D.C.
Events in Washington · 13 guests

41' Meridian Sedan Yacht for Charter in Washington, D.C.

5.0
$300+/hour
High Demand
 DMV’s 12 passenger Luxury Party Yacht Silverton Convertible
Events in Washington · 12 guests

DMV’s 12 passenger Luxury Party Yacht Silverton Convertible

5.0
$399/hour
$350hr | 9 Guests | Sport Regal Boat
Events in Washington · 9 guests

$350hr | 9 Guests | Sport Regal Boat

5.0
Superowner
$350/hour
2023 Yamaha AR190 - Perfect Day on the Water!
Powerboats in Virginia Beach · 7 guests

2023 Yamaha AR190 - Perfect Day on the Water!

5.0
$200/hour
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95+/hour
Hospitality at sea with Crownline 252 EX Deck Boat In Stone Harbor
Powerboats in Stone Harbor · 6 guests

Hospitality at sea with Crownline 252 EX Deck Boat In Stone Harbor

5.0
$129+/hour
Amazing SeaRay 260 Sundancer for Charter in DC
Powerboats in Washington · 6 guests

Amazing SeaRay 260 Sundancer for Charter in DC

5.0
$160/hour
Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included
Sailing in Saint Michaels · 6 guests

Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

New
$585/hour
$300hr | 8 Guests | Sport Boat
Events in Washington · 8 guests

$300hr | 8 Guests | Sport Boat

5.0
Superowner
$285/hour
Experience Colonial Beach in Style with SeaRay 220 Sundeck Bowrider Adventure!
Powerboats in Colonial Beach · 6 guests

Experience Colonial Beach in Style with SeaRay 220 Sundeck Bowrider Adventure!

5.0
$180/hour

Chesapeake Bay Reviews

  1. SF

    Sierra

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Captain Alberto and Grace were incredibly welcoming and accommodating during our time on their boat. Captain Alberto taught us all about sailing and we really enjoyed being involved with helping sail the boat. My friend group had such a great time; would recommend! We will definitely be back!

  2. ML

    Mike

    Hospitality at sea with Crownline 252 EX Deck Boat In Stone Harbor

    Beau was a total professional and knew all the history of the houses along the bay. Perfect timing for the sunset and everything. My wife grew up cruising Stone Harbor and she could not have been more happy with this cruise. 5 stars to Beau!!!

  3. KT

    Katerina

    41' Meridian Sedan Yacht for Charter in Washington, D.C.

    We had an absolutely great time! The boat itself is great, solid sound system, spacious and the upstairs is amazing for cruising. Trenton was a great captain. Would totally tent this boat again for a special occasion!

  4. RM

    Richard

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt. Alberto and his wife were awesome hosts! They were totally flexible about our schedule and it was great to hear about his prior sailing experiences. It was great to be with such an experienced host! We will definitely book with them in the future!!

  5. MK

    Michael

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt Alberto is great. Very knowledgeable and very pleasant. He lets you participate in manning the boat as much as you want and is especially good and introducing new sailors to the glorious activity. Highly recommend!

  6. MB

    Maya

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt Alberto and his wife were SO AMAZING!! They taught us how to sail and we sailed across the Chesapeake. Their boat is beautiful and their company is great. I highly recommend everyone book if they are looking to sail in the Annapolis area for a few hours, learn about sailing, and have a relaxing time.