Search Eastern Shore Cottage Rentals from CA $142
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Eastern Shore Cottages

Shore Point Cottages
Shore Point Cottages
9.4 out of 10, Exceptional, (204)

Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (244)

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, (176)

Dog-Friendly Westover Cottage w/ River Access!
Dog-Friendly Westover Cottage w/ River Access!
9.8 out of 10, Exceptional, (8)

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, (117)

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, (136)

Be persuaded to experience this vintage cottage by the Sassa
Be persuaded to experience this vintage cottage by the Sassa
9.4 out of 10, Exceptional, (8)

Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
8.4 out of 10, Very good, (48)
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
Other property types in Eastern Shore

Majestic Hotel & Apartments
Majestic Hotel & Apartments
6.6 out of 10, (187)

Shore Point Cottages
Shore Point Cottages
9.4 out of 10, Exceptional, (204)

Saint Tropez
Saint Tropez
9.0 out of 10, Wonderful, (91)
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.
Find out more about Eastern Shore
Find out more about Eastern Shore
Eastern Shore Cottages information
Number of reviews | 1,238 |
---|---|
Accommodation | 27 Cottages |
Lowest Price | CA $142 |
Highest Price | CA $195 |
Recent Reviews in Eastern Shore
Recent Reviews in Eastern Shore

Grand Hotel Ocean City Oceanfront
5/5 Excellent
"Had a lovely time."
A verified traveller stayed at Grand Hotel Ocean City Oceanfront
Posted 8 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
- Cottages in Ocean City
- Cottages in Perryville
- Cottages in Galena
- Cottages in North East
- Cottages in Elkton
- Cottages in Chestertown
- Cottages in Grasonville
- Cottages in Easton
- Cottages in Tilghman
- Cottages in Cambridge
- Cottages in St. Michaels
- Cottages in Stevensville
- Cottages in Berlin
- Cottages in Snow Hill
- Cottages in Salisbury
- Cottages in Bishopville
Top Cottages in Other Destinations
More Accommodation Types in Eastern Shore
- Condo Rentals in Eastern Shore
- Vacation Homes in Eastern Shore
- Apartments in Eastern Shore
- Motels in Eastern Shore
- B&B in Eastern Shore
- Cabin Rentals in Eastern Shore
- Farmstay in Eastern Shore
- Houseboats in Eastern Shore
- Aparthotels in Eastern Shore
- Resorts in Eastern Shore
- Villas in Eastern Shore
- Guest Houses in Eastern Shore
- Chalets in Eastern Shore
- Condo Resorts in Eastern Shore
- Inns in Eastern Shore
- Lodges in Eastern Shore
- Hotels
All Accommodation Types
Be inspired: Top Cottages destinations in 2025
- Algonquin Park Cottages
- Jasper National Park Cottages
- Tofino Cottages
- Cultus Lake Cottages
- Waterton Park Cottages
- Sunshine Coast Cottages
- Hope Cottages
- Radium Hot Springs Cottages
- Kananaskis Cottages
- Wasaga Beach Cottages
- Calgary Cottages
- Harrison Hot Springs Cottages
- Moncton Cottages
- Northern Ontario Cottages
- Kingston Cottages
- Mont-Tremblant Cottages
- Chilliwack Cottages
- Kenora Cottages
- Halifax Cottages
- Collingwood Cottages
More ways to book
Expedia's Latest Trends
Hotels
Flights
Packages