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Find The Best Boat Rentals in Chesapeake, Virginia.

4.9(Average of 100 reviews in this area)
Get set to boat with the GetMyBoat Guide to Chesapeake
1 - 24 of 33 listings
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Chesapeake Bay · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Chesapeake Bay · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$125hour
Melges 32 - The Ultimate Racing Experience
Sailing in Chesapeake Bay · 8 guests

Melges 32 - The Ultimate Racing Experience

5.0
Superowner
$200hour
38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia
Events in Chesapeake Bay · 6 guests

38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia

5.0
$450day
Fishing Charter on 38' Dawson Sportfish Yacht in Norfolk, Virginia
Fishing in Chesapeake Bay · 6 guests

Fishing Charter on 38' Dawson Sportfish Yacht in Norfolk, Virginia

5.0
$725day
🌊Double Jet Ski Rental🐟Twice the fun!!⚓A party on the water☀🌞☀
Water Sports in Chesapeake Bay · 3 guests

🌊Double Jet Ski Rental🐟Twice the fun!!⚓A party on the water☀🌞☀

5.0
$499day
22' Cape Craft 2200 DC Powerboat in Virginia Beach!
Powerboats in Chesapeake Bay · 6 guests

22' Cape Craft 2200 DC Powerboat in Virginia Beach!

5.0
$100hour
Sweetwater Pontoon Boat for Rent in Virginia Beach 6 Adults FREE GAS
Powerboats in Chesapeake Bay · 6 guests

Sweetwater Pontoon Boat for Rent in Virginia Beach 6 Adults FREE GAS

4.9
$100hour
Charter a Boat for Exciting Tour and Watersports in Norfolk, Virginia!
Powerboats in Chesapeake Bay · 6 guests

Charter a Boat for Exciting Tour and Watersports in Norfolk, Virginia!

5.0
$250hour
Fishing Kayak: 10' Sit On Top (3 available)
Adventures in Chesapeake Bay · 1 guest

Fishing Kayak: 10' Sit On Top (3 available)

5.0
$25day
Duffy Electric Boat Rental in Norfolk, Virginia
Powerboats in Chesapeake Bay · 8 guests

Duffy Electric Boat Rental in Norfolk, Virginia

5.0
$200hour
Bonito Fishing Boat Rental in Virginia Beach | 4 Adults | Free Gas
Powerboats in Chesapeake Bay · 4 guests

Bonito Fishing Boat Rental in Virginia Beach | 4 Adults | Free Gas

New
$100hour
Luxury Pontoon tours Serving Broad Bay Va Beach and Waterside Norfolk
Powerboats in Chesapeake Bay · 6 guests

Luxury Pontoon tours Serving Broad Bay Va Beach and Waterside Norfolk

5.0
$225hour
Brand New 2022 Avalon Tritoon!!!!!!
Powerboats in Chesapeake Bay · 6 guests

Brand New 2022 Avalon Tritoon!!!!!!

5.0
$250hour
Inshore/Offshore Fishing Trip in Norfolk/VA Beach With Captain Lou
Fishing in Chesapeake Bay · 6 guests

Inshore/Offshore Fishing Trip in Norfolk/VA Beach With Captain Lou

5.0
$160hour
Dolphin, Whale Watching, and Leisure Cruises
Chesapeake Bay · 6 guests

Dolphin, Whale Watching, and Leisure Cruises

5.0
$125hour
2022 Glastron Gx 210 Charters Servicing VA beach and Norfolk!
Powerboats in Chesapeake Bay · 6 guests

2022 Glastron Gx 210 Charters Servicing VA beach and Norfolk!

New
$250hour
Proline 23ft Center Console Fishing Boat for Charter in Suffolk
Fishing in Chesapeake Bay · 7 guests

Proline 23ft Center Console Fishing Boat for Charter in Suffolk

5.0
$250hour
Pearson 26 Coastal Sailboat in Norfolk
Sailing in Chesapeake Bay · 6 guests

Pearson 26 Coastal Sailboat in Norfolk

5.0
$60hour
Book this new, 8 person Suntracker Pontoon
Powerboats in Chesapeake Bay · 8 guests

Book this new, 8 person Suntracker Pontoon

5.0
$175hour
JETSKI TOURING IN YORKTOWN
Water Sports in Chesapeake Bay · 2 guests

JETSKI TOURING IN YORKTOWN

New
$50hour
JETSKI TOURING IN HAMPTON
Water Sports in Chesapeake Bay · 1 guest

JETSKI TOURING IN HAMPTON

4.0
$50hour
Personal Jet Ski Rentals in Virginia Beach, Virginia
Water Sports in Chesapeake Bay · 2 guests

Personal Jet Ski Rentals in Virginia Beach, Virginia

New
$149hour
Chaparral 21 H2O Sport Bowrider Rental in Virginia Beach, Virginia
Powerboats in Chesapeake Bay · 12 guests

Chaparral 21 H2O Sport Bowrider Rental in Virginia Beach, Virginia

New
$99hour

Chesapeake Reviews

  1. AW
    ALEX
    22' Cape Craft 2200 DC Powerboat in Virginia Beach!

    Great experience with Max from beginning to end. Took 2 people and 1 dog to False Cape. Super communicative and happy to work with our schedule and requests. He was on time, the boat was nice and he was all around just a nice guy to talk with. No issues and would recommend a boat trip with Max to anyone!

  2. CH
    Cyndi
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    My family of 5 had a wonderful day sailing with Bill to celebrate my husband's 40th birthday. Bill was very knowledgeable and excellent at explaining things to my children, even letting them each take the helm. We felt very at ease and safe our entire trip. I am already recommending him to friends.

  3. LN
    Linda
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    Mom, Dad, & three GROWN children went out on a wonderful outing with Captain Bill. He was a gracious host & his beautiful sailboat was spectacular! Enjoyed the experience immensely & seriously considering sailing lessons next spring. His boat was not only in immaculate condition but very comfortable for all five adults (plus the amiable captain). We were thrilled to see dolphins and hear about the area's history. We sailed 14.9 memorable miles. I gave a 5 star rating because the ratings don't go to 10. Honestly, how does one rate a great memory that lasts a lifetime? We weren't sure if the weather was going to be a wash out for a few days out, but Captain Bill kept in contact via email with weather updates and was extremely accommodating to what would work best for us. The weather wasn't what one would call picture perfect but I thought it was awesome having so much of the water to ourselves. We only saw one other sailboat. This was an exhilarating experience with a knowledgeable captain and I can't recommend him enough!

  4. JM
    Josh
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    I had my four children with me ages 5 to 12 the captain was very kind and understanding to them teaching them new things my son it was comfortable taking the helm and the captain enjoy teaching him the other kids not so much but that was okay however not to be prejudiced because they are my children but they are exceptionally good kids my youngest commented that she was upset she would not be seeing Captain bill the next day and on how much she liked him. we will be back to sail in August we learned about the wind the ocean and how to read it wheeler and practical knowledge and history of the area The boat was beautiful the captain was awesome it was a great day my kids will remember forever I am not one to give A+ review without truly meaning it

  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. SR
    Shannon
    Melges 32 - The Ultimate Racing Experience

    The boat was in perfect condition, ready for anything we could ask for. Doug sails and races on a weekly basis, often in this particular boat, so his feel for the boat, the wind, and the waters we sailed in are well honed. The boat is forgiving, and Doug was unflappable. An encouraging beginner experience, and very fast under experienced guidance. I did not hope for as good an experience, and cannot offer a higher endorsement. Top marks.

Boating Guide - Chesapeake

Find top rated boat rentals in Chesapeake, Virginia.

Chesapeake, Virginia is a great place to rent a boat. You can rent or charter a small motorboat, sailboat, houseboat, or even a yacht. Take in the beautiful scenery and spend quality time with your friends and family while having the perfect day on the water. From birthday celebrations and bachelor or bachelorette parties to family vacations, Chesapeake, Virginia is the perfect boat rental destination.

Using GetMyBoat to rent your next boat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat has 33 listings for boating experiences in Chesapeake with 100 reviews.

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