Cruises By Owner - Vacation Rentals in Northern Chesapeake Bay

Cass-Away Luxury Houseboat From US $171
         

10.0 (104 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Sailboat Experience in Annapolis From US $270
         

8.8 (5 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • Pet Friendly
Cass-N-Reel Luxury Houseboat From US $169
         

10.0 (47 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Luxe Houseboat: Breathtaking Skyline 360 Views From US $631
         

10.0 (22 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • Pool
Luxe Houseboat with Epic 360 Views of Baltimore Harbor From US $562
         

10.0 (11 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • Pool
Annapolis Boat Life - Overnight Stays From US $278
         

10.0 (1 Review)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Lovin’ Life ! From US $250
         

10.0 (1 Review)
Boat Rental
  • Air Conditioner
  • TV
  • Balcony/Terrace

Luxury Places to Stay in Northern Chesapeake Bay

Over 10000+ Luxury Places to Stay in or Near Northern Chesapeake Bay
Sailor's Sunrise Cottage - Chesapeake Bay From US $10,616
         

9.4 (54 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
2 bedroom 2 bath Townhouse From US $5,800
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Sports/Activities

Top-Rated Vacation Rentals with a Pool in Northern Chesapeake Bay

Over 3045+ Top-Rated Vacation Rentals with a Pool in or Near Northern Chesapeake Bay
Family and Pet-Friendly, Waterfront with Pier From US $275
         

10.0 (265 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Stunning Waterfront Cottage with Breathtaking Views! From US $449
         

10.0 (220 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Peaceful Cambridge Home on Jenkins Creek From US $371
         

10.0 (213 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Fabulous, Historic One BR Capitol Hill Apartment From US $177
         

10.0 (190 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Heart of the City - HalfBlock to METRO - Columbia Heights. From US $70
         

10.0 (162 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Northern Chesapeake Bay

Over 5402+ Pet-Friendly Vacation Rentals in or Near Northern Chesapeake Bay
Great Location with 2 King beds 2 queen beds From US $225
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Hummingbird Inn From US $331
         

|
10.0 (86 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Eastern Shore beach cottage get-away From US $327
         

10.0 (139 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Colorful Suite in CapitolHill+ Free Parking From US $130
         

9.4 (74 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Northern Chesapeake Bay

Over 2122+ Large Vacation Homes & Villas in or Near Northern Chesapeake Bay
Baydream Believer From US $1,025
         

10.0 (87 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Pentagon City Luxury Apartment From US $126
         

5.8 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
USNA Luxury Home, parking, pet friendly From US $910
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Multi-Generational Waterfront Retreat with Pool! From US $833
         

10.0 (70 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks From US $947
         

Wheelchair Accessible Vacation Homes in Northern Chesapeake Bay

Over 4569+ Wheelchair Accessible Vacation Homes in or Near Northern Chesapeake Bay
Bluebird Suites DC Financial District From US $161
         

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8.9 (44 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Oaks Waterfront From US $505
         

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10.0 (41 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Downtown 2BR in Woodmont Triangle | Steps to Metro From US $245
         

6.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Woodmont Triangle| Pet-friendly 1BR | nr Glen Echo Park From US $143
         

9.6 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Stay in the landmark Lighthouse! From US $373
         

10.0 (108 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
New Downtown Annapolis Condo With Free Parking From US $368
         

10.0 (36 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Northern Chesapeake Bay Varoom and Airbnb Places to Stay Under $200

Over 6204+ Northern Chesapeake Bay Varoom and Airbnb Places to Stay Under $200
Designer Fashion Loft 1 Bedroom Apartment -Royalty Homes From US $137
         

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5.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Internet
Newly renovated Gem of a Georgetown Home From US $170
         

9.6 (51 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Inn at Huntingfield Creek From US $173
         

|
10.0 (59 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Brand new and modern apartment on Red Line! From US $154
         

10.0 (60 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Beautiful Federal Hill home! From US $195
         

9.4 (49 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Northern Chesapeake Bay

Over 9342+ Instantly Bookable Vacation Homes in or Near Northern Chesapeake Bay
2BR - New Renovation with AC, Dishwasher, Laundry From US $173
         

10.0 (4 Reviews)
Apartment
  • TV
  • Security/Safety
  • Wellness Facilities
PERFECT LOCATION in the heart of history From US $387
         

10.0 (215 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Rare find! Chic cottage, salt water heated pool May 15-Oct15. From US $871
         

About Northern Chesapeake Bay Vacation Rentals

With more than 38 Northern Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cruisesbyowner and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Northern Chesapeake Bay.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruisesbyowner Northern Chesapeake Bay, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Northern Chesapeake Bay. Places to stay near Northern Chesapeake Bay are 169.19 ft² on average, with prices averaging $512 a night.

Cruisesbyowner makes it easy and safe to find and compare vacation rentals in Northern Chesapeake Bay with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Northern Chesapeake Bay

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Use these Quick Filters to Find a Vacation Rental in Northern Chesapeake Bay

Pro Tip: Cruisesbyowner makes it easy to compare the best listings on Cruisesbyowner homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruisesbyowner homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Northern Chesapeake Bay.

Weather in Northern Chesapeake Bay

View the weather forecast for Northern Chesapeake Bay before booking your Northern Chesapeake Bay Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F