Chestertown Cottages
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Cottages in Chestertown
Your Annapolis Waterfront retreat - ready for a winter getaway!
Annapolis MD
With a stay at this cottage in Annapolis (West Annapolis), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial Stadium.
Kitchen
Free WiFi
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall MD
With a stay at this cottage in Rock Hall, you'll be a 2-minute walk from Waterman’s Museum and 13 minutes by foot from Ferry Park.
Kitchen
Washer
Secluded Cozy Cottage in Historic Downtown
Annapolis MD
$495 nightly
The price is $564 total per night
$564 total
Mar 9 - Mar 10
Total with taxes and fees
With a stay at this cottage in Annapolis (Historic District), you'll be within a 15-minute walk of U.S. Naval Academy and 14 Fleet Street.
Kitchen
Washer
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Stevensville MD
With a stay at this cottage in Stevensville, you'll be within a 5-minute drive of Romancoke Wharf County Park and Chesapeake Bay.
Kitchen
Washer
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Earleville MD
Located in Earleville, this cottage is in a rural location, within a 15-minute drive of Earleville Wildlife Management Area and Earleville Wildlife Management Area.
Kitchen
Washer
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Centreville MD
With a stay at this cottage in Centreville, you'll be on the waterfront, and 6.5 mi (10.5 km) from Queenstown Premium Outlets and 6.9 mi (11.1 km) from Queenstown Harbor Golf Links.
Kitchen
Washer
The Heron's Nest at Atlantic Marina
Pasadena MD
When you stay at this cottage in Pasadena, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.
Pool
Kitchen
Rock Creek Cottage, Waterfront, Serene Views
Pasadena MD
With a stay at this cottage in Pasadena (Riviera Beach), you'll be within a 10-minute drive of Compass Pointe Golf Courses and Fort Smallwood Park.
Kitchen
Washer
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Rock Hall MD
With a stay at this cottage in Rock Hall, you'll be within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Pool
Free WiFi
Cozy, unique, historic registered cottage on the Corsica River!
Centreville MD
With a stay at this cottage in Centreville, you'll be within a 15-minute drive of Earle Landing and Queenstown Premium Outlets.
Kitchen
Washer
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.
Chestertown Cottages essential information
Accommodation | 62 Cottages |
|---|---|
Lowest Price | $564 |
Highest Price | $665 |
Popular accommodation | Your Annapolis Waterfront retreat - ready for a winter getaway!, Peaceful getaway convenient to local amenities including beach, boating & food, Secluded Cozy Cottage in Historic Downtown, Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly, Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay , Secluded Waterfront Cottage on 200 acre farm near Queenstown, The Heron's Nest at Atlantic Marina, Rock Creek Cottage, Waterfront, Serene Views, Charming cottage with Pool Access and WiFi in lovely Rock Hall, Cozy, unique, historic registered cottage on the Corsica River!, Eastern Shore beach cottage get-away, Chesapeake Cottages- 2 Quaint Waterfront Retreats |