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Chester, Virginia Boat Rentals and Yacht Charters

Page 1 of 124 listings

2022 Stingray 231DC, Richmond, Va
Powerboats in Richmond · 6 guests

2022 Stingray 231DC, Richmond, Va

New
$185/hour
2023 Edgewater Dual Console family fun and fishing boat.
Powerboats in Richmond · 10 guests

2023 Edgewater Dual Console family fun and fishing boat.

5.0
$175/hour
Nautique G23 one Lake Anna with Boathouse Experience
Powerboats in Richmond · 12 guests

Nautique G23 one Lake Anna with Boathouse Experience

5.0
$165/hour
18' Center Console Pocket Rocket fishing boat.
Fishing in Deltaville · 4 guests

18' Center Console Pocket Rocket fishing boat.

New
$325/day
2017 South Bay Pontoon Boat for 12 passengers at Dukes Creek Marina
Powerboats in Richmond · 12 guests

2017 South Bay Pontoon Boat for 12 passengers at Dukes Creek Marina

5.0
$70/hour
24’ Godfrey Sweetwater Pontoon on Lake Anna
Powerboats in Richmond · 12 guests

24’ Godfrey Sweetwater Pontoon on Lake Anna

5.0
$80/hour
22’ SunTracker Party Barge on Lake Anna
Powerboats in Richmond · 10 guests

22’ SunTracker Party Barge on Lake Anna

5.0
$80+/hour
Starting at $50 HR | 16ft Center Console | York River | Fishing license included
Powerboats in Gloucester Point · 4 guests

Starting at $50 HR | 16ft Center Console | York River | Fishing license included

5.0
$50/hour
Yamaha Jet Boat – 10 Seater Adventure on the Water
Powerboats in Richmond · 10 guests

Yamaha Jet Boat – 10 Seater Adventure on the Water

5.0
$100/hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117+/hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
2023 Sea-Doo GTI 170: Ride the Wave of Adventure!
Water Sports in Richmond · 3 guests

2023 Sea-Doo GTI 170: Ride the Wave of Adventure!

5.0
$150/hour
MasterCraft Wakeboarding boat for rent in the hampton roads area of Virginia
Water Sports in Newport News · 8 guests

MasterCraft Wakeboarding boat for rent in the hampton roads area of Virginia

New
$150/hour
2021 Sea Fox 226 dual console
Events in Deltaville · 8 guests

2021 Sea Fox 226 dual console

5.0
$76+/hour
Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509
Sailing in Deltaville · 8 guests

Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509

New
$524+/day
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
Melges 24 - One Design Racing Experience
Sailing in Hampton · 5 guests

Melges 24 - One Design Racing Experience

5.0
Superowner
$100/hour
Proline 23ft Center Console Fishing Boat for Charter in Suffolk
Fishing in Hampton · 6 guests

Proline 23ft Center Console Fishing Boat for Charter in Suffolk

5.0
$250/hour
Powerful, Luxury Tritoon w/ 150HP & All the Toys at Beautiful Lake Gaston!
Powerboats in North Carolina · 13 guests

Powerful, Luxury Tritoon w/ 150HP & All the Toys at Beautiful Lake Gaston!

5.0
$64/hour
44ft ''Four Winds'' Yacht for Fishing/Cruising/Sightseeing in Hampton, Virginia
Events in Hampton · 19 guests

44ft ''Four Winds'' Yacht for Fishing/Cruising/Sightseeing in Hampton, Virginia

4.0
$275/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
Enjoy the sights of Colonial Beach, VA ! Come boat with us!
Events in Colonial Beach · 6 guests

Enjoy the sights of Colonial Beach, VA ! Come boat with us!

5.0
$180/hour
40ft Evans Fishing Charter Boat in Colonial Beach
Fishing in Kinsale · 6 guests

40ft Evans Fishing Charter Boat in Colonial Beach

New
$650/day
Charter a Regal 400 Commodore Express Cruiser in Hampton for Up to 6 Guests
Powerboats in Hampton · 6 guests

Charter a Regal 400 Commodore Express Cruiser in Hampton for Up to 6 Guests

New
$300/hour

Chester Reviews

  1. YT

    Yen

    24’ Godfrey Sweetwater Pontoon on Lake Anna

    Great service. Personable and responsive. Would 100% use again for our boating needs!!

  2. EH

    Elizabeth

    22’ SunTracker Party Barge on Lake Anna

    Our experience with Joe and his boat could not have been better. From the beginning, Joe's professionalism and communication were excellent. Joe instilled the utmost confidence and followed through flawlessly, which made the entire experience stress free. The boat itself was in fantastic condition and ran like a dream. We were able to tube off the back and anchor at swim spots no problem. Delivery and pick up were quick and painless due to Joe's expert trailering skills. I'd highly recommend renting from Joe and hope to do so again in the future.

  3. Matthew

    Matthew

    Yamaha Jet Boat – 10 Seater Adventure on the Water

    First off, the owner is extremely great at communicating. And it made the experience very easy. To review the experience, We recently rented a Yamaha jet boat for a family outing, and it was absolutely fantastic! From start to finish, the experience exceeded our expectations. The boat was sleek, powerful, and incredibly easy to drive—even for someone without much boating experience. One of the highlights of our day was tubing—what a thrill! The boat had more than enough speed to keep things exciting, and the smooth handling made it easy to navigate even with kids in tow. We also anchored for a swim, and the swim platform made getting in and out of the water a breeze. The onboard audio system was a huge bonus. Crisp, clear sound with plenty of volume made it feel like we had our own floating party. Whether we were cruising or relaxing, the music added so much to the vibe. Overall, this Yamaha jet boat delivered on every level—performance, comfort, and fun. Highly recommend for families or groups looking to make amazing memories on the water!

  4. JP

    John

    Let's Go Sail in Gloucester Point, Virginia

    Captain Bill was a fantastic host for our inaugural sailing adventure in the York River out of Gloucester Point, VA. We booked him for a Saturday afternoon in June for a 2:30 to 5:30 cruise and it was everything we could have asked for and more. He explained the region's waters and relation to the Chesapeake Bay as well as the naval and nautical history of the area in addition to teaching us about his boat and how to sail it properly. We wanted to be immersed in the experience and he let us be very hands on, giving direction for assisting with deploying the sails, commanding the helm, reading the wind and performing the tacking maneuvers while being at the helm. We also had a chance to relax on the forward section of the deck as Bill took over, he passed our libations to us and helped us enjoy the experience of sailing while soft music played that even invited an interaction with one of the regions local dolphin who accompanied and entertained us for well over a half an hour on our return up the river. What an awesome way to spend an afternoon.

  5. DH

    Dan

    Let's Go Sail in Gloucester Point, Virginia

    Bill was awesome. Very communicative leading up to the sail with weather, directions, and other logistical specifics. The trip left and returned on time, Bill was very knowledgeable about the boat and the area, let my wife and I take the helm several times and the boat was in great condition. Would totally sail with Cpt Bill again.

  6. BS

    Bill

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    I highly recommend a sail with Captain Bill. The entire experience was exciting and relaxing at the same time. Whether an experienced sailor or a novice with boats, just being on the open water will refresh and invigorate. 5 ⭐️⭐️⭐️⭐️⭐️