Chesapeake Bay Cottage Rentals
Cottage
10.0(307 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
£210/Night
7 Nights - £1,468
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1323.96 ft²
Oceanfront
Spa- Fireplace/Heating
Ocean View
£74/Night
7 Nights - £521
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
£534/Night
7 Nights - £3,740
Cottage
10.0(277 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
£137/Night
7 Nights - £961
House
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
527.43 ft²
- Fireplace/Heating
- Parking
Internet
Child Friendly
£122/Night
7 Nights - £856
Cottage
10.0(184 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£225/Night
7 Nights - £1,579
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1280.91 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Ocean View
£296/Night
7 Nights - £2,073
Cottage
10.0(161 Reviews)
2 Bedrooms
1 Bath
6 Guests
1300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£143/Night
7 Nights - £1,002
House
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
753.47 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
£133/Night
7 Nights - £928
Cottage
10.0(147 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Private Pool- Oceanfront
- Fireplace/Heating
Pool
£643/Night
7 Nights - £4,498
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
1797.57 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
£283/Night
7 Nights - £1,980
Cottage
10.0(126 Reviews)
2 Bedrooms
1 Bath
8 Guests
963 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£343/Night
7 Nights - £2,402
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
Accomack County
Frequently Asked Questions About Chesapeake Bay Rental Cottages
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.
- Family and Pet-Friendly, Waterfront with Pier
- Annapolis waterfront "tiny house" in garden setting
- Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
- The Yellow Cottage on Harness Creek
- Private 1300 sq ft Cottage in Historic Yorktown-w/trolley access
- Eastern Shore beach cottage get-away
- Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
- Blissful Retreat In Rock Hall
2. How many Cottages are available in Chesapeake Bay?
Currently, the total number of properties listed by RBO in 2026 is over 744 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)
2 Bedrooms
1 Bath
8 Guests
1087.15 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
£281/Night
7 Nights - £1,970
Cottage
10.0(84 Reviews)
2 Bedrooms
1 Bath
5 Guests
576 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£199/Night
7 Nights - £1,391
Cottage
10.0(83 Reviews)
1 Bedroom
1 Bath
4 Guests
850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£229/Night
7 Nights - £1,606
Cottage
10.0(67 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£615/Night
7 Nights - £4,302
Cottage
10.0(51 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£209/Night
7 Nights - £1,459
Cottage
10.0(39 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£392/Night
7 Nights - £2,744
Cottage
10.0(24 Reviews)
2 Bedrooms
2 Baths
5 Guests
944 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£205/Night
7 Nights - £1,435
Cottage
10.0(18 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£769/Night
7 Nights - £5,385
Cottage
10.0(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£303/Night
7 Nights - £2,121
Cottage
10.0(15 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£269/Night
7 Nights - £1,883
Cottage
10.0(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Pet Friendly
£282/Night
7 Nights - £1,977
Cottage
10.0(10 Reviews)
2 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£566/Night
7 Nights - £3,961
