Sunset Island Ocean City - Vacation Rentals in Chesapeake Bay

Great Location with 2 King beds 2 queen beds From US $225
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Arlington 1BR apartment Near DC & Pentagon From US $149
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Cottage on a Private Island in the York River From US $227
         

10.0 (372 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
PERFECT LOCATION in the heart of history From US $515
         

10.0 (223 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Chesapeake Bay

Over 10000+ Luxury Places to Stay in or Near Chesapeake Bay
2 bedroom 2 bath Townhouse From US $5,800
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area

Top-Rated Vacation Rentals with a Pool in Chesapeake Bay

Over 7157+ Top-Rated Vacation Rentals with a Pool in or Near Chesapeake Bay
Family and Pet-Friendly, Waterfront with Pier From US $381
         

10.0 (268 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Peaceful Cambridge Home on Jenkins Creek From US $398
         

10.0 (213 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Barclay Cottage From US $285
         

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10.0 (213 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
NESTLED IN PRIME CAPITOL HILL LOCATION - STEPS AWAY TO EVERYTHING! From US $287
         

Pet-Friendly Vacation Rentals in Chesapeake Bay

Over 9101+ Pet-Friendly Vacation Rentals in or Near Chesapeake Bay
Bluebird Suites DC Financial District From US $161
         

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8.9 (44 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hummingbird Inn From US $362
         

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10.0 (89 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Eastern Shore beach cottage get-away From US $403
         

10.0 (139 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Kingsbay Mansion Bayhouse From US $958
         

10.0 (39 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chesapeake Bay

Over 4133+ Large Vacation Homes & Villas in or Near Chesapeake Bay
Baydream Believer From US $1,669
         

10.0 (88 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Pentagon City Luxury Apartment From US $126
         

5.8 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks From US $1,209
         

Classically Current - Chesapeake Properties From US $758
         

9.8 (86 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Beautiful Lindal Cedar Home Near Beach! Private Pool! From US $489
         

Wheelchair Accessible Vacation Homes in Chesapeake Bay

Over 6948+ Wheelchair Accessible Vacation Homes in or Near Chesapeake Bay
Churchill Living City Center From US $285
         

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New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Oaks Waterfront From US $538
         

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10.0 (41 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Entire Home w/pool, walk to beach From US $1,011
         

Chesapeake Bay Vacation Rentals and Airbnb Places to Stay Under $200

Over 9423+ Chesapeake Bay Vacation Rentals 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 (52 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Marvel's on the Creek From US $200
         

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10.0 (166 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Brand new and modern apartment on Red Line! From US $171
         

10.0 (62 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Colonial Beach Bay house with views & canoe From US $185
         

9.0 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Fells Point Gem/In The Heart of Fells Point From US $150
         

9.8 (205 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Chesapeake Bay

Over 16540+ Instantly Bookable Vacation Homes in or Near Chesapeake Bay
The Sparrows Nest - in downtown Sparrows Point From US $236
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Crestwood Manor - An urban oasis with Free Parking From US $278
         

New
Hotel
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
SANDY HILL SUNSETS From US $252
         

10.0 (74 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Designated Smoking Area
All the comforts of home! From US $290
         

10.0 (73 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Chesapeake Bay Vacation Rentals

With more than 27986 Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Sunsetislandoceancity 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 Chesapeake Bay.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sunsetislandoceancity 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 Chesapeake Bay. Places to stay near Chesapeake Bay are 733.07 ft² on average, with prices averaging US $365 a night.

Sunsetislandoceancity makes it easy and safe to find and compare vacation rentals in 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 Chesapeake Bay

Type Count
Vacation Homes 11793
Holiday Apartments 7676
Hotels 3439
Resorts 756
Cottages 629
B&B 438
Villas 288
Cabin Rentals 96
Others 87
Hostels 18
Ski Chalet Rentals 5

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

Pro Tip: Sunsetislandoceancity makes it easy to compare the best listings on Sunsetislandoceancity homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sunsetislandoceancity 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 Chesapeake Bay.

Weather in Chesapeake Bay

View the weather forecast for Chesapeake Bay before booking your 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

Chesapeake Bay Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chesapeake Bay?
How many vacation rentals are available in Chesapeake Bay?

Currently, the total number of properties listed in 2026 is over 27986 in the Chesapeake Bay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesapeake Bay.