Chesapeake Bay Accommodations
House
10.0(159 Reviews)
2 Bedrooms
2 Baths
4 Guests
1425 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
CA $526/Night
7 Nights - CA $3,683
Bed & Breakfast
10.0(89 Reviews)
23 Bedrooms
24 Baths
60 Guests
- Balcony/Terrace
- Parking
Air Conditioner
Internet
CA $410/Night
7 Nights - CA $2,873
Bed & Breakfast
10.0(215 Reviews)
1 Bedroom
1 Bath
Spa
Pool- Balcony/Terrace
Breakfast
CA $377/Night
7 Nights - CA $2,637
Apartment
10.0(89 Reviews)
1 Bedroom
1 Bath
5 Guests
650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $310/Night
7 Nights - CA $2,167
House
10.0(17 Reviews)
3 Bedrooms
2 Baths
7 Guests
1302.43 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
CA $229/Night
7 Nights - CA $1,601
Apartment
10.0(67 Reviews)
1 Bedroom
1 Bath
4 Guests
450 ft²
Private Pool
Hot Tub- Fireplace/Heating
- Pool
CA $249/Night
7 Nights - CA $1,746
Bed & Breakfast
10.0(10 Reviews)
1 Bedroom
1 Bath
4 Guests
398.26 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
CA $330/Night
7 Nights - CA $2,307
House
10.0(64 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
CA $383/Night
7 Nights - CA $2,681
House
10.0(8 Reviews)
3 Bedrooms
2 Baths
10 Guests
10763.91 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
CA $1,408/Night
7 Nights - CA $9,856
House
10.0(54 Reviews)
2 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
CA $397/Night
7 Nights - CA $2,781
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
2 Baths
6 Guests
850.35 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
CA $451/Night
7 Nights - CA $3,160
House
10.0(45 Reviews)
2 Bedrooms
2 Baths
6 Guests
1725 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $318/Night
7 Nights - CA $2,228
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
Norfolk - Virginia Beach
Washington
District of Columbia
Virginia Beach
Northwest
Baltimore
Anne Arundel County
Accomack County
Chincoteague
Norfolk
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:
- Captivating Chesapeake experience
- 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
- PERFECT LOCATION in the heart of history
- Live the "Life on a Sandbar" in a beachfront bungalow! with ODU Football Tickets
- BOAT, FISH, CRAB, SWIM, RELAX! WELCOME TO YOUR EASTERN SHORE ESCAPE!
- Charming Historic Annapolis Home With Two Off-street Parking Places!
- Island Life! Kent Island Waterfront with Pool-Bring your boat!
- Ultraclean Family Waterfront Home Annapolis Area - 200+ Top Reviews!
2. How many Accommodations are available in Chesapeake Bay?
Currently, the total number of properties listed by RBO in 2026 is over 21383 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
House
10.0(8 Reviews)
3 Bedrooms
1 Bath
8 Guests
1097.92 ft²
Oceanfront- Spa
- Fireplace/Heating
- Ocean View
CA $387/Night
7 Nights - CA $2,710
Apartment
10.0(39 Reviews)
1 Bedroom
1 Bath
2 Guests
480 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
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Apartment
10.0(37 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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Apartment
10.0(35 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
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Cabin
10.0(30 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $568/Night
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House
10.0(29 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
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Villa
10.0(25 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
CA $636/Night
7 Nights - CA $4,453
House
10.0(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $666/Night
7 Nights - CA $4,659
House
10.0(22 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $404/Night
7 Nights - CA $2,826
Cabin
10.0(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $332/Night
7 Nights - CA $2,323
Apartment
10.0(22 Reviews)
1 Bedroom
1 Bath
4 Guests
512 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $233/Night
7 Nights - CA $1,634
Apartment
10.0(16 Reviews)
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
CA $261/Night
7 Nights - CA $1,829
