Best Family Escapes - 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
Cottage on a Private Island in the York River From US $247
         

10.0 (364 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
PERFECT LOCATION in the heart of history From US $463
         

10.0 (220 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
Entire Twnhouse 2bdrms 3Bthrm 2Qbeds 2Levls Fncd Bkyard From US $4,830
         

Top-Rated Vacation Rentals with a Pool in Chesapeake Bay

Over 7000+ Top-Rated Vacation Rentals with a Pool in or Near Chesapeake Bay
Family and Pet-Friendly, Waterfront with Pier From US $333
         

10.0 (265 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Peaceful Cambridge Home on Jenkins Creek From US $382
         

10.0 (213 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Barclay Cottage From US $106
         

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10.0 (205 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chesapeake Bay

Over 9064+ 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 $368
         

10.0 (139 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Kingsbay Mansion Bayhouse From US $816
         

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

Large Vacation Homes & Villas in Chesapeake Bay

Over 4085+ Large Vacation Homes & Villas in or Near Chesapeake Bay
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
Baydream Believer From US $1,392
         

10.0 (87 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks From US $999
         

Classically Current - Chesapeake Properties From US $572
         

9.8 (86 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Beautiful Lindal Cedar Home Near Beach! Private Pool! From US $652
         

Wheelchair Accessible Vacation Homes in Chesapeake Bay

Over 6903+ 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 $1,007
         

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

Over 9608+ 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
Inn at Huntingfield Creek From US $173
         

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10.0 (61 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Colonial Beach Bay house with views & canoe From US $185
         

9.0 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic Home Close to Main Street From US $197
         

9.6 (55 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Chesapeake Bay

Over 16342+ Instantly Bookable Vacation Homes in or Near Chesapeake Bay
The Camper at The Pines Horse Farm From US $232
         

SANDY HILL SUNSETS From US $248
         

10.0 (74 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Designated Smoking Area
All the comforts of home! From US $256
         

10.0 (72 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Chesapeake Bay Vacation Rentals

With more than 27957 Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bestfamilyescapes 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 Bestfamilyescapes 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 747.46 ft² on average, with prices averaging $361 a night.

Bestfamilyescapes 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 11681
Holiday Apartments 7767
Hotels with Suites 3456
Resorts 752
Cottages 618
B&B 449
Villas 290
Cabin Rentals 97
Others 97
Hostels 18
Ski Chalet Rentals 4

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

Pro Tip: Bestfamilyescapes makes it easy to compare the best listings on Bestfamilyescapes homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bestfamilyescapes 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 27957 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.