Old Mansions - Vacation Rentals in Chesapeake Bay

Property Image From $225
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $904
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Property Image From $137
         

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5.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Internet
Property Image From $207
         

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10.0 (160 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Property Image From $161
         

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8.9 (44 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $300
         

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10.0 (96 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Property Image From $285
         

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New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Chesapeake Bay

Over 4959+ Luxury Places to Stay in or Near Chesapeake Bay
Property Image From $4,830
         

Property Image From $2,994
         

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8.6 (144 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Property Image From $2,729
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Accessibility
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Chesapeake Bay

Over 1364+ Top-Rated Vacation Rentals with a Pool in or Near Chesapeake Bay
Property Image From $250
         

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10.0 (65 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Property Image From $173
         

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10.0 (56 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Property Image From $505
         

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10.0 (38 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Property Image From $229
         

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10.0 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $258
         

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10.0 (6 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Property Image From $790
         

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10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $94
         

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10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chesapeake Bay

Over 1483+ Pet-Friendly Vacation Rentals in or Near Chesapeake Bay
Property Image From $119
         

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1.0 (39 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $344
         

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10.0 (82 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $118
         

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7.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $483
         

Property Image From $164
         

Property Image From $414
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $229
         

9.0 (14 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $77
         

Large Vacation Homes & Villas in Chesapeake Bay

Over 525+ Large Vacation Homes & Villas in or Near Chesapeake Bay
Property Image From $126
         

5.8 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Property Image From $910
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $360
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $664
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From $271
         

Property Image From $896
         

9.6 (51 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Chesapeake Bay

Over 1744+ Wheelchair Accessible Vacation Homes in or Near Chesapeake Bay
Property Image From $138
         

Property Image From $738
         

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10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Property Image From $291
         

Property Image From $274
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Property Image From $106
         

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New
Apartment
  • Parking
  • Pool
  • Wheelchair Accessible
Property Image From $282
         

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10.0 (1 Review)
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
Property Image From $157
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $315
         

9.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Chesapeake Bay Varoom and Airbnb Places to Stay Under $200

Over 2506+ Chesapeake Bay Varoom and Airbnb Places to Stay Under $200
Property Image From $60
         

9.6 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Property Image From $194
         

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10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • TV
Property Image From $83
         

9.0 (4 Reviews)
Apartment
  • Air Conditioner
Property Image From $170
         

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10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • View
Property Image From $86
         

8.0 (79 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Child Friendly
Property Image From $197
         

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9.8 (74 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Balcony/Terrace
Property Image From $143
         

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8.5 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Child Friendly
Property Image From $48
         

5.5 (4 Reviews)
Hostel
  • Parking
  • Pet Friendly
  • Balcony/Terrace

Instantly Bookable Vacation Homes in Chesapeake Bay

Over 88+ Instantly Bookable Vacation Homes in or Near Chesapeake Bay
Property Image From $173
         

10.0 (4 Reviews)
Apartment
  • TV
  • Security/Safety
  • Wellness Facilities
Property Image From $458
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $298
         

9.8 (20 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Wellness Facilities
Property Image From $178
         

9.8 (6 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

About Chesapeake Bay Vacation Rentals

With more than 4968 Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Old Mansions 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 Old Mansions 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 815.02 ft² on average, with prices averaging $277 a night.

Old Mansions 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
Hotels with Suites 1956
Vacation Homes 1538
Holiday Apartments 1142
B&B 120
Resorts 54
Villas 43
Cottages 36
Cabin Rentals 19
Hostels 18
Others 16
Ski Chalet Rentals 2

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

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