Chestertown Vacation Rentals

Name: Historic Annapolis Home 1.5 blocks from center of town.
Address: Annapolis

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Vacation Rentals in Chestertown

Pet-Friendly Home on Chester River w/ Dock!

When you stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Washington College.

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Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

3512 Gough Street, Baltimore, MD

With a stay at this vacation home in Baltimore (Highlandtown), you'll be a 4-minute drive from Johns Hopkins Hospital and 8 minutes from Baltimore Cruise Terminal.

Washer

Dryer

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.

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Washer

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.

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Washer

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.

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Washer

Waterfront house with amazing views. Top of the Chesapeake

Located in Perryville, this vacation home is on the waterfront, within a 15-minute drive of Garrett Island Beach and Upper Bay Museum.

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Washer

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.

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Washer

Waterfront Oasis w/ Private Dock, 3BR/2BA

Located in Middle River, this vacation home is on the waterfront, within a 15-minute drive of Gunpowder Falls State Park and Freestate Gun Range.

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Pet friendly

Charming Historic Townhouse Steps From USNA

This vacation home is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval Academy.

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Washer

Cozy 2br home w/ parking in downtown Annapolis

$307

includes taxes & fees

$273 per night

Jan 13 - Jan 14, 2025

A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.

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Washer

Waterfront family resort Lodge with private pier, game room and bar

Located in Centreville, this vacation home is on a river, within a 10-minute drive of Hazel Miner Monument and Earle Landing.

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Washer

Historic Annapolis Home 1.5 blocks from center of town.

A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.

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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.