Chester Cottages
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Cottages in Chester
![Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun](https://images.trvl-media.com/lodging/84000000/83960000/83955900/83955892/e64cf201_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
With a stay at this cottage in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of Sandy Point State Park and U.S. Naval Academy.
Hot Tub
Breakfast included
![Cottage at Goose Neck Point](https://images.trvl-media.com/lodging/85000000/84160000/84158600/84158519/a61901f1_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cottage at Goose Neck Point
Located in Royal Oak, this cottage is on the waterfront, within a 15-minute drive of St. Michaels Winery and St. Michaels Museum.
![Waterfront home with beach on the Chesapeake Dog-Friendly](https://images.trvl-media.com/lodging/91000000/90910000/90909800/90909712/7886974a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Waterfront home with beach on the Chesapeake Dog-Friendly
When you stay at this cottage in Annapolis, you'll be on the beach, within a 10-minute walk of Annapolis Sailing School and Annapolis Landing Marina.
![Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA](https://images.trvl-media.com/lodging/34000000/33970000/33965500/33965405/a1d6df97_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
With a stay at this cottage, you'll be centrally located in Edgewater, within a 15-minute drive of Sand Point Marsh and South River Golf Links.
![John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/811a0e85_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
With a stay at this cottage in St. Michaels, you'll be a 5-minute walk from St. Michaels Museum and 7 minutes by foot from St. Michaels Winery.
![Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/3df2f268_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
With a stay at this cottage in St. Michaels, you'll be a 5-minute walk from Chesapeake Bay Maritime Museum and 6 minutes by foot from St. Michaels Museum.
Kitchen
Washer
![Eastern Shore beach cottage get-away](https://images.trvl-media.com/lodging/34000000/33490000/33489100/33489089/d201362f_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Eastern Shore beach cottage get-away
With a stay at this cottage in Rock Hall, you'll be a 1-minute walk from Ferry Park and 13 minutes by foot from Waterman’s Museum.
![Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.](https://images.trvl-media.com/lodging/77000000/76790000/76789900/76789882/f06c74be_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
This cottage is 19.1 mi (30.8 km) from U.S. Naval Academy and 3.3 mi (5.2 km) from Franklin Point State Park.
![The Heron's Nest at Atlantic Marina](https://images.trvl-media.com/lodging/37000000/36300000/36290700/36290653/9c5e6ebd_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Heron's Nest at Atlantic Marina
Located in Pasadena, this cottage is on the waterfront, within a 10-minute drive of Fort Smallwood Park and Compass Pointe Golf Courses.
![Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/3245ad2c_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
With a stay at this cottage in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
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.
Chester Cottages essential information
Accommodation | 56 Cottages |
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Lowest Price | |
Highest Price | |
Popular accommodation | Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun, Cottage at Goose Neck Point, Waterfront home with beach on the Chesapeake Dog-Friendly, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Eastern Shore beach cottage get-away, Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC., The Heron's Nest at Atlantic Marina, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, MEMORIAL DAY SPECIAL - 3 DAY MINIMUM 10% OFF ROOM CHARGE , Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels |