Chesapeake Bay Accommodations
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
GB £248/Night
For 7 Nights GB £1,737
60 Guests
23 Bedrooms
24 Bathrooms
Group Friendly
Bed & Breakfast
- Balcony/Terrace
- Parking
- Air Conditioner
GB £215/Night
For 7 Nights GB £1,503
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
GB £161/Night
For 7 Nights GB £1,130
1900 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £300/Night
For 7 Nights GB £2,099
1302.43 ft²
7 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
GB £120/Night
For 7 Nights GB £838
1425 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
GB £245/Night
For 7 Nights GB £1,717
1097.92 ft²
8 Guests
3 Bedrooms
1 Bathroom
House
- Oceanfront
- Spa
- Fireplace/Heating
GB £167/Night
For 7 Nights GB £1,171
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
GB £204/Night
For 7 Nights GB £1,425
398.26 ft²
4 Guests
1 Bedroom
1 Bathroom
Bed & Breakfast
- Fireplace/Heating
- View
- Parking
GB £172/Night
For 7 Nights GB £1,207
900 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
GB £106/Night
For 7 Nights GB £741
10763.91 ft²
10 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
GB £737/Night
For 7 Nights GB £5,156
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £110/Night
For 7 Nights GB £770
Why Choose Rent By Owner for your Chesapeake Bay Accommodations?
What makes our Accommodations 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 Accommodations
What's our booking process?
Our platform allows you to browse a curated selection of accommodations. 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 Accommodations Amenities
What amenities can you expect?
Our Accommodations 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
Accomack County
Frequently Asked Questions about Chesapeake Bay Accommodations
1. What are the top Accommodations 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 Accommodations in Chesapeake Bay:
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Captivating Chesapeake experience
- Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
- Private Apt. in Historic Home: Walk to Monuments, Museums & Convention Center.
- Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds
- Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
- PERFECT LOCATION in the heart of history
- Stunning Waterfront Cottage in the Sailing Capital of the World!
2. How many Accommodations are available in Chesapeake Bay?
Currently, the total number of properties listed by RBO in 2026 is over 20989 in the Chesapeake Bay area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Chesapeake Bay.
More Rentals You May Like Near Chesapeake Bay
850.35 ft²
6 Guests
1 Bedroom
2 Bathrooms
Bed & Breakfast
- Fireplace/Heating
- View
- Parking
GB £236/Night
For 7 Nights GB £1,653
1300 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
GB £307/Night
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650 ft²
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
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780 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £151/Night
For 7 Nights GB £1,060
1000 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £200/Night
For 7 Nights GB £1,402
339 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
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- Oceanfront
- Fireplace/Heating
- Ocean View
GB £134/Night
For 7 Nights GB £941
450 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
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- Private Pool
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- Fireplace/Heating
GB £125/Night
For 7 Nights GB £877
1 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £224/Night
For 7 Nights GB £1,567
9 Guests
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2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
GB £169/Night
For 7 Nights GB £1,182
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £125/Night
For 7 Nights GB £877
1000 ft²
6 Guests
2 Bedrooms
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Ocean View
Boat Rental
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £223/Night
For 7 Nights GB £1,559
