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Browse Chesapeake Bay Boat Rentals.

5.0(Average of 1,869 reviews in this area)
Learn more about boating in Chesapeake Bay
Page 1 of 8 (179 listings)
2021 24' Sylvan L3 DLZ Pontoon Boat
Powerboats in Riviera Beach · 12 guests

2021 24' Sylvan L3 DLZ Pontoon Boat

5.0
$149hour
$350 weekdays | $450 weekends | 14 ppl | Catamaran
Powerboats in Washington · 14 guests

$350 weekdays | $450 weekends | 14 ppl | Catamaran

5.0
Superowner
Best of 2022
$350hour
46' Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 8 guests

46' Catamaran Charter with Water Toys - Annapolis, MD

5.0
$213hour
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
$175hour
$400HR Weekdays | $750 HR Weekend| 12-20 PPL | Sea Ray 450 Express Bridge
Events in Washington · 20 guests

$400HR Weekdays | $750 HR Weekend| 12-20 PPL | Sea Ray 450 Express Bridge

5.0
Superowner
Best of 2022
$375hour
2016 Regal 31' CruiseThe Inner Harbor, Annapolis, Hart Miller Island, discount weekday pricing
Powerboats in Annapolis · 8 guests

2016 Regal 31' CruiseThe Inner Harbor, Annapolis, Hart Miller Island, discount weekday pricing

4.9
Best of 2022
$225hour
Come and enjoy the beautiful DC view on the Potomac river aboard Sancha
Events in Washington · 12 guests

Come and enjoy the beautiful DC view on the Potomac river aboard Sancha

5.0
$375hour
🚤 Bonito Center Console Party Boat Rental Cheap Fishing Charter Tube FREE GAS⛽️
Powerboats in Virginia Beach · 4 guests

🚤 Bonito Center Console Party Boat Rental Cheap Fishing Charter Tube FREE GAS⛽️

5.0
$30-83hour
Hurricane 23ft Deckboat for Private Charters in Ocean City
Powerboats in Ocean City · 6 guests

Hurricane 23ft Deckboat for Private Charters in Ocean City

5.0
$100person
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.7
$165hour
⚓️🛥️Premium Private Yachting Experience🍹☀️
Events in Washington · 6 guests

⚓️🛥️Premium Private Yachting Experience🍹☀️

4.9
Superowner
Best of 2022
$200-299hour
Instant Book
🚤Pontoon Boat Rentals in Virginia Beach Party Cruise Tubing 8 Adults FREE GAS ⛽
Powerboats in Virginia Beach · 8 guests

🚤Pontoon Boat Rentals in Virginia Beach Party Cruise Tubing 8 Adults FREE GAS ⛽

4.9
$32-100hour
$150HR | 2-3 people | JetSki
Water Sports in Alexandria · 2 guests

$150HR | 2-3 people | JetSki

5.0
Superowner
Best of 2022
$150hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
Best of 2022
$138-150hour
Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
Powerboats in Washington · 6 guests

Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

5.0
$160-190hour
$300 HR | 7 people | Brand New Cruiser Sea Ray SLX 310
Powerboats in Washington · 7 guests

$300 HR | 7 people | Brand New Cruiser Sea Ray SLX 310

5.0
Superowner
Best of 2022
$300hour
2018 Chaparral 21 H2O Sport ,tow tube available
Powerboats in Virginia Beach · 8 guests

2018 Chaparral 21 H2O Sport ,tow tube available

5.0
$100hour
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
$160hour
41' Lagoon Catamaran in Maryland, United States
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland, United States

5.0
Superowner
Best of 2022
$320hour
Great Center Console for rent in Ocean City
Powerboats in Ocean City · 6 guests

Great Center Console for rent in Ocean City

4.8
$150hour
$300 per hour | 8 PPl | Drone ✈️ footage + Grill+ water Toys
Powerboats in Washington · 9 guests

$300 per hour | 8 PPl | Drone ✈️ footage + Grill+ water Toys

New
Superowner
Best of 2022
$300hour
BEST DAY EVER! CLEAN BOAT! HIGHLY EXPERIENCED CAPTAIN! $325/hr WEEKENDS $275 WEEKDAYS
Events in Washington · 6 guests

BEST DAY EVER! CLEAN BOAT! HIGHLY EXPERIENCED CAPTAIN! $325/hr WEEKENDS $275 WEEKDAYS

5.0
Superowner
Best of 2022
$325hour
Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ
Powerboats in Wildwood · 6 guests

Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ

5.0
$275hour
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 12 guests

31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

5.0
$250hour

Chesapeake Bay Boat Rentals

One of the best experiences you can have on the east coast of the United States is a boat rental on the Chesapeake Bay. Book a sailboat charter for an all-encompassing tour of the bay and see the stunning shoreline from the water. Boat tours and fishing on the Chesapeake Bay are not only great for tourists but are also fabulous experiences for life-long locals to enjoy in the summer. There are many water tours and types of boating experiences you can have on the Chesapeake Bay. Choose from pontoon rentals, sailboat rentals, bareboat rentals, yacht charters and even houseboat rentals.

Chesapeake Bay Reviews

  1. MS
    Monique
    46' Catamaran Charter with Water Toys - Annapolis, MD

    Deren & Kristal were excellent hosts! We had a lovely day sailing the Chesapeake. They were very communicative and timely with their responses and were flexible with our parties needs and wants. What an excellent experience! Would highly recommend their boat.

  2. NC
    Nicki
    $350 weekdays | $450 weekends | 14 ppl | Catamaran

    My friends and I had THE BEST time boating with AJ’s team. They were all so accommodating, friendly and eager to ensure we had a great time. The communication from booking to boating was seamless and thorough. AJ was so responsive and helpful. I would 100% recommend anyone to book with them, they will go above and beyond to make sure you have an amazing time!

  3. JK
    Jennifer
    Hurricane 23ft Deckboat for Private Charters in Ocean City

    Jake and Devin were absolutely amazing. Their professionalism and knowledge of the area truly created a unique and special experience for us. We had 4 children under the age of 11 and they were so kind and patient with them. Thank you for a fun morning and great memories.

  4. JC
    Jessica
    ⚓️🛥️Premium Private Yachting Experience🍹☀️

    Had an amazing time with captain Shane! The weather wasn’t the best, but Shane always had our safety in mind and we had a lot of fun regardless of the rain! Definitely recommend doing this, the route is the best and you can play your own music!

  5. WC
    Whitney
    Experience the Serenity of Sailing SV Magic

    We had an awesome trip with Josh. He was very flexible with timing and knowledgeable about sailing. We were able to take our engagement photos on Josh’s boat with his help and input on lighting/backgrounds. It was a wonderful experience we will never forget!

  6. BM
    Bernadette
    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

    Capt Michael is amazing. His boat is beautiful and well maintained. He is friendly, professional and knows how to Captain. He was very flexible and understanding when we had a change of plans and dropped off some of our crew at another location. We highly recommend him for your fun day out on the bay and we will be booking him again!

Boating Guide - Chesapeake Bay

Chesapeake Bay Boat Rentals

One of the best experiences you can have on the east coast of the United States is a boat rental on the Chesapeake Bay. Book a sailboat charter for an all-encompassing tour of the bay and see the stunning shoreline from the water. Boat tours and fishing on the Chesapeake Bay are not only great for tourists but are also fabulous experiences for life-long locals to enjoy in the summer. There are many water tours and types of boating experiences you can have on the Chesapeake Bay. Choose from pontoon rentals, sailboat rentals, bareboat rentals, yacht charters and even houseboat rentals.

GetMyBoat has 179 listings for boating experiences in Chesapeake Bay with 1,869 reviews.

Search Chesapeake Bay