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Find The Best Boat Rentals in Chesapeake, Virginia.

Page 1 of 124 listings

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
38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!
Events in Virginia Beach · 13 guests

38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!

4.9
Superowner
$199+/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
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
38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia
Fishing in Norfolk · 6 guests

38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia

5.0
$450/day
2022 Avalon Tritoon!
Powerboats in Virginia Beach · 10 guests

2022 Avalon Tritoon!

5.0
$199/hour
38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Hampton, Virginia!
Events in Hampton · 13 guests

38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Hampton, Virginia!

5.0
Superowner
$199+/hour
Sunset Boat Rides in Va Beach
Powerboats in Virginia Beach · 6 guests

Sunset Boat Rides in Va Beach

5.0
$225/hour
Melges 24 - One Design Racing Experience
Sailing in Hampton · 5 guests

Melges 24 - One Design Racing Experience

5.0
Superowner
$100/hour
Instant Book
Fishing Charter on 38' Dawson Sportfish Yacht in Norfolk, Virginia
Fishing in Norfolk · 6 guests

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

5.0
$94+/hour
Watersports Charter! Tubing · Wakeboarding · Waterskiing
Powerboats in Virginia Beach · 6 guests

Watersports Charter! Tubing · Wakeboarding · Waterskiing

5.0
$213+/hour
Luxury Pontoon tours Serving Broad Bay Va Beach and Waterside Norfolk
Powerboats in Virginia Beach · 6 guests

Luxury Pontoon tours Serving Broad Bay Va Beach and Waterside Norfolk

5.0
$188/hour
Party Cruises & Fishing Trips in Virginia Beach
Fishing in Norfolk · 6 guests

Party Cruises & Fishing Trips in Virginia Beach

5.0
$170+/hour
Instant Book
Inshore/Offshore Fishing Trip in Norfolk/VA Beach With Captain Lou
Fishing in Norfolk · 6 guests

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

5.0
$146+/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
Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA
Sailing in Norfolk · 6 guests

Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA

New
$725/day
Fisherman’s Dream: 38ft Dawson Sportfish in Norfolk, VA!
Fishing in Norfolk · 6 guests

Fisherman’s Dream: 38ft Dawson Sportfish in Norfolk, VA!

New
$170/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 luxury, comfort, and versatility with Interlude and CruiseVB
Events in Virginia Beach · 12 guests

Experience luxury, comfort, and versatility with Interlude and CruiseVB

New
$350/hour
🚤 2010 Bayliner 195 F-19 – Power, Comfort, and Fun on the Water!
Powerboats in Virginia Beach · 5 guests

🚤 2010 Bayliner 195 F-19 – Power, Comfort, and Fun on the Water!

New
$155/hour
Instant Book
Great for water sports "tubing/ski" and cruising the bay for romantic outings!
Powerboats in Virginia Beach · 7 guests

Great for water sports "tubing/ski" and cruising the bay for romantic outings!

New
$225/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
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
Book this new, 6 person Suntracker Pontoon
Powerboats in Virginia Beach · 6 guests

Book this new, 6 person Suntracker Pontoon

5.0
Snoozed - Active 02 Jan 2026

Chesapeake Reviews

  1. KB

    Kayah

    38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!

    We had an awesome time on the boat it was the perfect size for a group of 11. If you the waves are too much the inside is perfect place to still enjoy the water with out feeling the motion

  2. AJ

    Arne

    38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!

    The experience was AWESOME!!! I booked a 2 hour tour with Captain Kody as a surprise for my husband’s Birthday and all of our family and friends had a BLAST. Didn’t realize how much fun it would be. Only thing I would do different, is book a longer tour 😂😂

  3. HS

    Heather

    2023 Yamaha AR190 - Perfect Day on the Water!

    My family and I had such a great time! Ameen made it comfortable and safe for me and our 2 teen boys. Teens can be hard to please but they are both excited to boat with ameen again. This is an excursion that you can mold to fit your style and it well worth it. Thanks guys!!!

  4. AN

    Adrea

    38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!

    I recently rented a boat for my birthday, and the experience on the water was absolutely fantastic. The boat ride was amazing, providing a fun and memorable day for me and my friends. We enjoyed the beautiful scenery and the smooth sailing, which made for a perfect celebration. Captain Dreux (Drew) was a complete vibe! He was friendly, and made us feel very welcomed. Would absolutely recommend requesting him as your captain!

  5. AJ

    April

    38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!

    We had an amazing experience with our captain Ron today in Virginia Beach! He was very accommodating and continuously went out of his way to make sure we had a great time. He was very down to earth and super fun!! I highly recommend this company and can’t wait for the next venture!

  6. 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.