Chesapeake Bay Cottage Rentals
Cottage
10.0(311 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $338/Night
7 Nights - US $2,364
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1323.96 ft²
Oceanfront- Parking
Spa
Ocean View
US $101/Night
7 Nights - US $707
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $725/Night
7 Nights - US $5,077
Cottage
10.0(287 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $230/Night
7 Nights - US $1,609
House
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
527.43 ft²
- Parking
Internet
Child Friendly
Sports/Activities
US $166/Night
7 Nights - US $1,162
Cottage
10.0(188 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $339/Night
7 Nights - US $2,372
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1280.91 ft²
Private Beach- Oceanfront
- Parking
- Ocean View
US $402/Night
7 Nights - US $2,814
Cottage
10.0(168 Reviews)
2 Bedrooms
1 Bath
6 Guests
1300 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $249/Night
7 Nights - US $1,746
House
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
753.47 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
US $180/Night
7 Nights - US $1,260
Cottage
10.0(150 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Private Pool- Oceanfront
- Parking
Pool
US $867/Night
7 Nights - US $6,070
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
2 Guests
1087.15 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $568/Night
7 Nights - US $3,975
Cottage
10.0(133 Reviews)
2 Bedrooms
1 Bath
8 Guests
963 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $529/Night
7 Nights - US $3,706
Why Choose Rent By Owner for your Chesapeake Bay Cottage Rentals?
What makes our Cottage Rentals 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 Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage rentals. 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 Cottage Rentals Amenities
What amenities can you expect?
Our Cottage Rentals 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
Northwest
Virginia Beach
Baltimore
Anne Arundel County
Northeast Virginia Beach
Alanton
Arlington
Chesapeake Bay Cottage Rentals Frequently Asked Questions
1. What are the top Cottages 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 Cottages in Chesapeake Bay:
- Cottage on a Private Island in the York River
- Adorable Cottage In The Heart Of The Old Beach Area, Close To The Boardwalk.
- The Yellow Cottage on Harness Creek
- Private 1300 sq ft Cottage in Historic Yorktown-w/trolley access
- Eastern Shore beach cottage get-away
- Blissful Retreat In Rock Hall
- Island Time Cottage
- Cozy island cottage with a Key West flair - CLOSEST TO THE BEACH!
- Lovely backyard cottage with easy access to metro, shops, dining!
- WATERFRONT COTTAGE, Only 5 years old, Located on Beautiful Taylor Creek
2. How many Cottages are available in Chesapeake Bay?
Currently, the total number of properties listed by RBO in 2026 is over 735 in the Chesapeake Bay area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Chesapeake Bay.
More Rentals You May Like Near Chesapeake Bay
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
1797.57 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $384/Night
7 Nights - US $2,688
Cottage
10.0(85 Reviews)
1 Bedroom
1 Bath
4 Guests
850 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $295/Night
7 Nights - US $2,066
Cottage
10.0(84 Reviews)
2 Bedrooms
1 Bath
5 Guests
576 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $310/Night
7 Nights - US $2,171
Cottage
10.0(69 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Parking
- Spa
- Balcony/Terrace
- Kitchen
US $602/Night
7 Nights - US $4,217
Cottage
10.0(51 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $345/Night
7 Nights - US $2,412
Cottage
10.0(43 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $583/Night
7 Nights - US $4,083
Cottage
10.0(27 Reviews)
2 Bedrooms
2 Baths
5 Guests
944 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $360/Night
7 Nights - US $2,521
Cottage
10.0(21 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $319/Night
7 Nights - US $2,235
Cottage
10.0(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $536/Night
7 Nights - US $3,751
Cottage
10.0(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $316/Night
7 Nights - US $2,215
Cottage
10.0(10 Reviews)
2 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,009/Night
7 Nights - US $7,062
Cottage
10.0(10 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $542/Night
7 Nights - US $3,794
