Photo by Patricia Knorr
Search Cottages in Chester
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Cottages in Chester
Compare 63 Cottages in Chester with updated reviews, rates, and availability.
Amazing views, short walks to great dining!
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (76)
Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (217)
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
10.0 out of 10, Exceptional, (81)
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (33)
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (7)
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (204)
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, (112)
The Heron's Nest at Atlantic Marina
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (286)
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 Chester
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (8)
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (205)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (23)
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.
Recent reviews of Chester hotels
Recent reviews of Chester hotels
5/5 Excellent
"Absolutely beautiful Inn "
A verified traveler stayed at Historic Inns of Annapolis
Posted 13 hours ago