Chesapeake Bay Resorts

New
8 Guests 2 Bathrooms
Resort
  • Hot Tub
  • Fireplace/Heating
  • Air Conditioner
£367/Night For 7 Nights £2,566
10.0
Exceptional
(1 Review)
678.13 ft² 4 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Private Pool
  • Oceanfront
  • Pool
£276/Night For 7 Nights £1,929
9.2
Exceptional
(545 Reviews)
1 Bathroom
Family Friendly Resort
  • Hot Tub
  • Spa
  • Pool
£161/Night For 7 Nights £1,127
New
4 Guests 1 Bathroom
Family Friendly Resort
  • Kitchen
  • Parking
  • Air Conditioner
£257/Night For 7 Nights £1,796
9.2
Exceptional
(113 Reviews)
40 Guests 14 Bathrooms
Ocean View Resort
  • Oceanfront
  • Fireplace/Heating
  • Pool
£155/Night For 7 Nights £1,087
10.0
Exceptional
(13 Reviews)
535 ft² 4 Guests 1 Bathroom
Family Friendly Resort
  • Fireplace/Heating
  • Pool
  • Kitchen
£119/Night For 7 Nights £833
9.2
Exceptional
(65 Reviews)
333.68 ft² 16 Guests 44 Bedrooms 3 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
£258/Night For 7 Nights £1,807
10.0
Exceptional
(2 Reviews)
1462 ft² 6 Guests 2 Bathrooms
Family Friendly Resort
  • Hot Tub
  • Spa
  • Fireplace/Heating
£322/Night For 7 Nights £2,253
9.2
Exceptional
(8 Reviews)
279.86 ft² 2 Guests 1 Bedroom 1 Bathroom
Apartment
  • Oceanfront
  • Spa
  • Fireplace/Heating
£227/Night For 7 Nights £1,591
10.0
Exceptional
(1 Review)
545 ft² 4 Guests 1 Bathroom
Family Friendly Resort
  • Fireplace/Heating
  • Pool
  • Kitchen
£103/Night For 7 Nights £722
9.1
Exceptional
(594 Reviews)
460.46 ft² 40 Guests 1 Bathroom
Ocean View Resort
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
£242/Night For 7 Nights £1,696
10.0
Exceptional
(1 Review)
585 ft² 4 Guests 1 Bathroom
Family Friendly Resort
  • Fireplace/Heating
  • Pool
  • Kitchen
£94/Night For 7 Nights £659

Why Choose Rent By Owner for your Chesapeake Bay Resorts?

What makes our Resorts special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Chesapeake Bay

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Other Places to Stay in Chesapeake Bay, MD

Frequently Asked Questions About Chesapeake Bay Resorts

2. How many Resorts are available in Chesapeake Bay?

Currently, the total number of properties listed by RBO in 2026 is over 792 in the Chesapeake Bay area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Chesapeake Bay. 

More Rentals You May Like Near Chesapeake Bay

9.1
Exceptional
(304 Reviews)
864.34 ft² 54 Guests 10 Bathrooms
Free Cancellation Resort
  • Private Pool
  • Fireplace/Heating
  • Pool
£110/Night For 7 Nights £768
9.8
Exceptional
(82 Reviews)
8 Guests 2 Bathrooms
Family Friendly Resort
  • Hot Tub
  • Spa
  • Fireplace/Heating
£222/Night For 7 Nights £1,557
9.8
Exceptional
(18 Reviews)
902 ft² 4 Guests 1 Bathroom
Family Friendly Resort
  • Hot Tub
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£113/Night For 7 Nights £789
9.6
Exceptional
(96 Reviews)
1242 ft² 8 Guests 2 Bathrooms
Family Friendly Resort
  • Hot Tub
  • Fireplace/Heating
  • Pool
£109/Night For 7 Nights £765
9.6
Exceptional
(26 Reviews)
1238 ft² 8 Guests 2 Bathrooms
Family Friendly Resort
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
£168/Night For 7 Nights £1,177
9.6
Exceptional
(4 Reviews)
8 Guests 2 Bathrooms
Family Friendly Resort
  • Hot Tub
  • Fireplace/Heating
  • Pool
£158/Night For 7 Nights £1,110
9.4
Exceptional
(122 Reviews)
1242 ft² 8 Guests 2 Bathrooms
Family Friendly Resort
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
£168/Night For 7 Nights £1,174
9.4
Exceptional
(40 Reviews)
1023 ft² 6 Guests 2 Bathrooms
Family Friendly Resort
  • Hot Tub
  • Fireplace/Heating
  • Pool
£139/Night For 7 Nights £972
9.4
Exceptional
(25 Reviews)
1238 ft² 8 Guests 2 Bathrooms
Family Friendly Resort
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
£158/Night For 7 Nights £1,110
9.4
Exceptional
(18 Reviews)
400 ft² 4 Guests 1 Bathroom
Family Friendly Resort
  • Fireplace/Heating
  • Pool
  • Kitchen
£120/Night For 7 Nights £838
9.2
Exceptional
(307 Reviews)
516 ft² 4 Guests 1 Bathroom
Family Friendly Resort
  • Private Pool
  • Hot Tub
  • Spa
£88/Night For 7 Nights £618
9.2
Exceptional
(218 Reviews)
1005 ft² 6 Guests 2 Bathrooms
Family Friendly Resort
  • Hot Tub
  • Spa
  • Fireplace/Heating
£119/Night For 7 Nights £837