Hotel Geres - Vacation Rentals in Chesapeake Bay

Cottage on a Private Island in the York River From US $227
         

10.0 (372 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
  • Parking
  • Pet Friendly
Barclay Cottage From US $265
         

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10.0 (215 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
PERFECT LOCATION in the heart of history From US $548
         

10.0 (225 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

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 7210+ Top-Rated Vacation Rentals with a Pool in or Near Chesapeake Bay
Fabulous, Historic One BR Capitol Hill Apartment From US $197
         

10.0 (191 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Heart of the City - HalfBlock to METRO - Columbia Heights. From US $74
         

10.0 (163 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3 From US $975
         

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks From US $1,209
         

Pet-Friendly Vacation Rentals in Chesapeake Bay

Over 9127+ Pet-Friendly Vacation Rentals in or Near Chesapeake Bay
Eastern Shore beach cottage get-away From US $492
         

10.0 (140 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
Anvil Campground From US $84
         

8.2 (38 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Kingsbay Mansion Bayhouse From US $934
         

10.0 (39 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Slack Tide by Seaside Vacations & Sales From US $333
         

9.8 (51 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Del Ray Designer Home walk to Shops, Cafes, Fun From US $501
         

9.6 (63 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Chesapeake Bay

Over 4150+ 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
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
         

Blue Bay - Chesapeake Properties From US $1,024
         

10.0 (57 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Chesapeake Bay

Over 6986+ 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
Fairfield Inn & Suites by Marriott Easton From US $167
         

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9.6 (376 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

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

Over 9516+ Chesapeake Bay Vacation Rentals and Airbnb Places to Stay Under $200
Newly renovated Gem of a Georgetown Home From US $170
         

9.6 (52 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
Wilson House Bed & Breakfast From US $141
         

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9.6 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Designated Smoking Area
  • TV
Cozy Fells Point Gem/In The Heart of Fells Point From US $150
         

9.8 (205 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Private garden apartment in historic Upper Fells Point From US $130
         

Instantly Bookable Vacation Homes in Chesapeake Bay

Over 16473+ Instantly Bookable Vacation Homes in or Near Chesapeake Bay
2BR - New Renovation with AC, Dishwasher, Laundry From US $173
         

10.0 (4 Reviews)
Apartment
  • TV
  • Security/Safety
  • Wellness Facilities
All the comforts of home! From US $389
         

10.0 (73 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
It’s All about the VIEW….and you ! From US $249
         

10.0 (69 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Beach Pines by Seaside Vacations & Sales From US $281
         

9.4 (30 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

About Chesapeake Bay Vacation Rentals

With more than 28077 Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hotelgeres 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 Hotelgeres 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 733.1 ft² on average, with prices averaging US $364 a night.

Hotelgeres 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 11844
Holiday Apartments 7744
Hotels 3440
Resorts 758
Cottages 628
B&B 437
Villas 290
Cabin Rentals 94
Others 63
Hostels 19
Ski Chalet Rentals 5

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

Pro Tip: Hotelgeres makes it easy to compare the best listings on Hotelgeres homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Hotelgeres 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 28077 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.