Chesapeake Bay Accommodations
House
10.0(392 Reviews)
2 Bedrooms
2 Baths
4 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $316/Night
7 Nights - US $2,214
Bed & Breakfast
10.0(89 Reviews)
23 Bedrooms
24 Baths
60 Guests
- Balcony/Terrace
- Parking
Air Conditioner
Internet
US $289/Night
7 Nights - US $2,022
Bed & Breakfast
10.0(209 Reviews)
1 Bedroom
1 Bath
Spa
Pool- Balcony/Terrace
Breakfast
US $133/Night
7 Nights - US $931
House
10.0(198 Reviews)
3 Bedrooms
2 Baths
10 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $444/Night
7 Nights - US $3,108
House
10.0(17 Reviews)
3 Bedrooms
2 Baths
7 Guests
1302.43 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
US $161/Night
7 Nights - US $1,127
House
10.0(153 Reviews)
2 Bedrooms
2 Baths
4 Guests
1425 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $332/Night
7 Nights - US $2,325
Bed & Breakfast
10.0(16 Reviews)
1 Bedroom
1 Bath
2 Guests
301.39 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- View
US $175/Night
7 Nights - US $1,227
House
10.0(115 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $274/Night
7 Nights - US $1,917
House
10.0(8 Reviews)
3 Bedrooms
2 Baths
10 Guests
10763.91 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $991/Night
7 Nights - US $6,937
House
10.0(114 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $142/Night
7 Nights - US $997
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
2 Baths
6 Guests
850.35 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $318/Night
7 Nights - US $2,224
House
10.0(112 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $143/Night
7 Nights - US $1,002
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
Anne Arundel County
Baltimore
Northeast Virginia Beach
Alanton
Arlington
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 21465 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.
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House
10.0(8 Reviews)
3 Bedrooms
1 Bath
8 Guests
1097.92 ft²
Oceanfront- Spa
- Fireplace/Heating
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US $316/Night
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House
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House
10.0(68 Reviews)
2 Bedrooms
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Apartment
10.0(64 Reviews)
1 Bedroom
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- Private Pool
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House
10.0(61 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
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House
10.0(60 Reviews)
1 Bedroom
1 Bath
2 Guests
339 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $203/Night
7 Nights - US $1,420
House
10.0(54 Reviews)
2 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $256/Night
7 Nights - US $1,789
House
10.0(54 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $164/Night
7 Nights - US $1,150
House
10.0(53 Reviews)
2 Bedrooms
1 Bath
4 Guests
1 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $301/Night
7 Nights - US $2,108
Boat Rental
10.0(53 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $276/Night
7 Nights - US $1,930
