Northern Chesapeake Bay Tours and Activities

A large suspension bridge over a calm body of water with a sunset in the background.

A sunset over a body of water with a bridge in the distance.

A sunset over a body of water with waves and a distant shoreline.

A suspension bridge with the sun setting behind it, reflecting on the water.

Fishing rods against a blue sky with clouds.

Visit Northern Chesapeake Bay

Things to do

Activities

Things to do

Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise

CA $48

per adult

90% of travellers recommend

Annapolis Harbor and U.S. Naval Academy Cruise

CA $48

per adult

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $42

per adult

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

CA $13

per traveller

80% of travellers recommend

Two Flight Indoor Skydiving Experience

CA $143

per traveller

94% of travellers recommend

Historic Annapolis Food Tour

CA $112

per adult

See all activities in Maryland

Plan a trip to see Northern Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.

Hotel Burg

Leesburg's Old and Historic District

Save 100% on your flight

CA $1,153

per person

Nov 19 - Nov 22

found 3 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Baltimore (BWI)

9.6/10 Exceptional! (128 reviews)

tiny tiny room with no closet- not sure what the “resort fee” was for- but it was in town and by a trail so that was nice. Was definitely not worth what we paid- but they get you with convenience i guess… very clean room.

Reviewed on Oct 16, 2026

One Sky Loft

Center City

CA $1,345

per person

Dec 26 - Dec 31

found 18 hours ago

Roundtrip flight included

Montreal (YUL) to Philadelphia (PHL)

9.2/10 Wonderful! (145 reviews)

This is my second stay at one sky loft this time in a bigger suite. It was beautiful, clean, spacious, private entrance with a rooftop balcony and views. I did put in a request for extra wash cloths the day I arrived because it was 4 people but didn't get them until the day before we were to leave. We had plenty of towels though. I will definitely stay again and again!

Reviewed on Oct 15, 2026

The Windsor Suites

Center City

CA $1,169

per person

Dec 26 - Dec 31

found 18 hours ago

Roundtrip flight included

Montreal (YUL) to Philadelphia (PHL)

8.8/10 Excellent! (3,295 reviews)

Best Lodging Options Near Northern Chesapeake Bay

Check availability on hotels close to Northern Chesapeake Bay

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville MD

Kent Island Resort

500 Kent Manor Dr Stevensville MD

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville MD

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville MD

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville MD

Graduate by Hilton Annapolis

126 West St Annapolis MD

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville MD

Historic Inns of Annapolis

58 State Circle Annapolis MD

See all 2,769 properties in Northern Chesapeake Bay

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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St. Leonard Vacation Rentals

Things to do in Maryland