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
Next weekend
In two weeks
In one month
In two 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)

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (4)
The price is ¥26,541
¥44,126 total
includes taxes & fees
Sep 3 - Sep 4

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
The price is ¥27,721
¥69,740 total
includes taxes & fees
Aug 28 - Aug 29

Soul Oasis - home on the Chesapeake Bay
Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (31)
The price is ¥22,118
¥46,421 total
includes taxes & fees
Sep 2 - Sep 3

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Comfortable & Private 2 Bedrm Cottage w/ King bed.
10.0 out of 10, Exceptional, (13)
The price is ¥20,827
¥52,371 total
includes taxes & fees
Sep 7 - Sep 8

Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
10.0 out of 10, Exceptional, (16)
The price is ¥25,777
¥39,817 total
includes taxes & fees
Sep 1 - Sep 2

Cozy Bay Cottage private backyard blocks from beach!
Cozy Bay Cottage private backyard blocks from beach!
9.0 out of 10, Wonderful, (38)
The price is ¥33,176
¥63,185 total
includes taxes & fees
Aug 31 - Sep 1

Bay Dream Believer Cottage on Beautiful East River Waterfront
Bay Dream Believer Cottage on Beautiful East River Waterfront
10.0 out of 10, Exceptional, (19)
The price is ¥34,651
¥67,820 total
includes taxes & fees
Aug 28 - Aug 29
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
Find out more about Chesapeake Bay
Find out more about Chesapeake Bay
Chesapeake Bay Cottages information
Number of reviews | 1,222 |
---|---|
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