Search Chesapeake Bay Cottage Rentals
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
In two weeks
In one month
In two months
In three months
Cottages in Chesapeake Bay
Our top choices for Chesapeake Bay cottages

Key West Cottages
Key West Cottages
9.8 out of 10, Exceptional, (437)

Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (255)

Lovely backyard cottage with easy access to metro, shops, dining!
Lovely backyard cottage with easy access to metro, shops, dining!
10.0 out of 10, Exceptional, (71)

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (184)

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (122)

The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (164)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (142)

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (119)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Top Chesapeake Bay Hotel Reviews

citizenM Washington DC Capitol
10/10 Excellent
Find out more about Chesapeake Bay
Find out more about Chesapeake Bay
Chesapeake Bay Cottages information
Number of reviews | 1,810 |
---|---|
Accommodation | 80 Cottages |
Lowest Price | ¥30,963 |
Highest Price | ¥73,725 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Cottages in Other Destinations
More Accommodation Types in Chesapeake Bay
- Vacation Homes in Chesapeake Bay
- Apartments in Chesapeake Bay
- Condo Rentals in Chesapeake Bay
- B&B in Chesapeake Bay
- Motels in Chesapeake Bay
- Aparthotels in Chesapeake Bay
- Resorts in Chesapeake Bay
- Cabin Rentals in Chesapeake Bay
- Guest Houses in Chesapeake Bay
- Hostels in Chesapeake Bay
- Villas in Chesapeake Bay
- Houseboats in Chesapeake Bay
- Castles in Chesapeake Bay
- Condo Resorts in Chesapeake Bay
- Inns in Chesapeake Bay
- Hotels
All Accommodation Types
Be inspired: Top Cottages destinations in 2025
- Cottages in Kusatsu
- Cottages in Gotemba
- Cottages in Kouri Island
- Cottages in Kamikochi
- Cottages in Asahikawa
- Cottages in Shodoshima
- Cottages in Numazu
- Cottages in Toyako
- Cottages in Rusutsu
- Cottages in Okinawa
- Cottages in North Okinawa
- Cottages in Hatsushima
- Cottages in Ishigaki
- Cottages in Himeji
- Cottages in Chatan
- Cottages in Mishima
- Cottages in Jozankei
- Cottages in Kofu
- Cottages in Biei
- Cottages in Fujinomiya
More ways to book
Expedia's Latest Trends
Hotels
Flights
Cars
Packages