Chesapeake Bay Resorts
8 Guests
2 Bathrooms
Resort
- Hot Tub
- Fireplace/Heating
- Air Conditioner
£367/Night
For 7 Nights £2,566
678.13 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Pool
- Oceanfront
- Pool
£276/Night
For 7 Nights £1,929
1 Bathroom
Family Friendly
Resort
- Hot Tub
- Spa
- Pool
£161/Night
For 7 Nights £1,127
4 Guests
1 Bathroom
Family Friendly
Resort
- Kitchen
- Parking
- Air Conditioner
£257/Night
For 7 Nights £1,796
40 Guests
14 Bathrooms
Ocean View
Resort
- Oceanfront
- Fireplace/Heating
- Pool
£155/Night
For 7 Nights £1,087
535 ft²
4 Guests
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Kitchen
£119/Night
For 7 Nights £833
333.68 ft²
16 Guests
44 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
£258/Night
For 7 Nights £1,807
1462 ft²
6 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Spa
- Fireplace/Heating
£322/Night
For 7 Nights £2,253
279.86 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Oceanfront
- Spa
- Fireplace/Heating
£227/Night
For 7 Nights £1,591
545 ft²
4 Guests
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Kitchen
£103/Night
For 7 Nights £722
460.46 ft²
40 Guests
1 Bathroom
Ocean View
Resort
- Private Pool
- Oceanfront
- Fireplace/Heating
£242/Night
For 7 Nights £1,696
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?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Chesapeake Bay
How to Book Your Chesapeake Bay Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
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.
Explore and book the perfect rental in Chesapeake Bay
Common Resorts Amenities
What amenities can you expect?
Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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
Maryland
Northern Chesapeake Bay
Washington
District of Columbia
Norfolk - Virginia Beach
Virginia Beach
Northwest
Baltimore
Anne Arundel County
Northeast Virginia Beach
Alanton
Arlington
Frequently Asked Questions About Chesapeake Bay Resorts
1. What are the top Resorts in Chesapeake Bay?
There are a lot of options in Chesapeake Bay. If you plan on staying in the Chesapeake Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Chesapeake Bay:
- Low Rates for The Historic Powhatan Resort
- OFFICIAL LISTING | Wyndham Old Town Alexandria 1 BR FREE WiFi & Metro Access!
- Wyndham Kingsgate, 3 BR Dlx - Sleeps 10, Indoor Pool! 25% Deposit, LOCAL HOST!
- 1 Bedroom Studio on the Virginia Beach waterfront
- Marriott's Manor Club at Ford's Colony - Many Weeks Available - Top Owner!
- Sun, Sand, and Surf! 2 Great Units with Full Kitchen, Oceanfront, Pool
- 2BR Retreat with 2 Oceanfront Balconies at Hilton Ocean Beach Club Resort
- Oceanfront Large 2BR/3BA Resort Suite ONE WEEK ONLY July 11-July 18 2026 Kitchen
- Marriott 2 bdrm 2 baths, minutes from Colonial Williamsburg downtown.
- Enjoy Breathtaking Beauty on the Chesapeake Bay
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
864.34 ft²
54 Guests
10 Bathrooms
Free Cancellation
Resort
- Private Pool
- Fireplace/Heating
- Pool
£110/Night
For 7 Nights £768
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Spa
- Fireplace/Heating
£222/Night
For 7 Nights £1,557
902 ft²
4 Guests
1 Bathroom
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
£113/Night
For 7 Nights £789
1242 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
£109/Night
For 7 Nights £765
1238 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Balcony/Terrace
£168/Night
For 7 Nights £1,177
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
£158/Night
For 7 Nights £1,110
1242 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Private Pool
- Hot Tub
- Fireplace/Heating
£168/Night
For 7 Nights £1,174
1023 ft²
6 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
£139/Night
For 7 Nights £972
1238 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Balcony/Terrace
£158/Night
For 7 Nights £1,110
400 ft²
4 Guests
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Kitchen
£120/Night
For 7 Nights £838
Enjoy our Colonial Style Resort in Williamsburg with Free parking, pool access, mini golf and tennis
516 ft²
4 Guests
1 Bathroom
Family Friendly
Resort
- Private Pool
- Hot Tub
- Spa
£88/Night
For 7 Nights £618
1005 ft²
6 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Spa
- Fireplace/Heating
£119/Night
For 7 Nights £837
