Inclusive Holidays - Vacation Rentals in Chesapeake Bay

Cottage on a Private Island in the York River From US $215
         

10.0 (359 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Great Location with 2 King beds 2 queen beds From US $225
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
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  • Pet Friendly
PERFECT LOCATION in the heart of history From US $447
         

10.0 (213 Reviews)
House
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  • TV

Luxury Places to Stay in Chesapeake Bay

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

9.4 (54 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Oasis near Metro: Arcade, Coffee, Parks From US $10,606
         

9.4 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Chesapeake Bay

Over 6678+ Top-Rated Vacation Rentals with a Pool in or Near 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
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  • Parking
  • Pool
Barclay Cottage B&B From US $359
         

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10.0 (201 Reviews)
Bed & Breakfast
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  • Pool

Pet-Friendly Vacation Rentals in Chesapeake Bay

Over 8519+ Pet-Friendly Vacation Rentals in or Near Chesapeake Bay
Eastern Shore beach cottage get-away From US $312
         

10.0 (138 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
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 $331
         

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10.0 (86 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Kingsbay Mansion Bayhouse From US $799
         

10.0 (39 Reviews)
House
  • 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 Chesapeake Bay

Over 3784+ Large Vacation Homes & Villas in or Near Chesapeake Bay
Baydream Believer From US $1,003
         

10.0 (87 Reviews)
House
  • Air Conditioner
  • Parking
  • View
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
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  • Parking
  • Pool
Classically Current - Chesapeake Properties From US $513
         

9.8 (86 Reviews)
House
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  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Chesapeake Bay

Over 6461+ Wheelchair Accessible Vacation Homes in or Near Chesapeake Bay
Churchill Living City Center From US $285
         

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New
Apartment
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  • Pet Friendly
The Oaks Waterfront From US $505
         

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10.0 (41 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Entire Home w/pool, walk to beach From US $895
         

Chesapeake Bay Varoom and Airbnb Places to Stay Under $200

Over 10529+ Chesapeake Bay Varoom and Airbnb Places to Stay Under $200
Newly renovated Gem of a Georgetown Home From US $170
         

9.6 (51 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Designer Fashion Loft 1 Bedroom Apartment -Royalty Homes From US $137
         

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5.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Internet
Charming 2-bedroom Cap Cod style cottage From US $185
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Brand new and modern apartment on Red Line! From US $150
         

10.0 (59 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

Instantly Bookable Vacation Homes in Chesapeake Bay

Over 15121+ Instantly Bookable Vacation Homes in or Near Chesapeake Bay
SANDY HILL SUNSETS From US $248
         

10.0 (74 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
All the comforts of home! From US $251
         

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

About Chesapeake Bay Vacation Rentals

With more than 26107 Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Inclusiveholidays 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 Inclusiveholidays 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 743.95 ft² on average, with prices averaging $328 a night.

Inclusiveholidays 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 10974
Holiday Apartments 7292
Hotels with Suites 3019
Resorts 739
Cottages 592
B&B 414
Villas 263
Others 95
Cabin Rentals 86
Hostels 17
Ski Chalet Rentals 3

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

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