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200 High Street

1. 200 High Street

 Chestertown, Maryland
Bright and open 2 bedroom apartment in the heart of downtown Chestertown
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Brampton Bed and Breakfast Inn

2. Brampton Bed and Breakfast Inn

 Chestertown, Maryland
Discover a historic and award-winning bed and breakfast in Chestertown, MD. This romantic inn is situated on 35 beautiful acres with glorious views and delicious breakfasts! Unforgettable rooms offer whirlpool tubs, fireplaces, and flat-screen TVs.
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Brittland Manor

3. Brittland Manor

 Chestertown, Maryland
From fields to rivers Brittland Estates personifies elegance in a rural setting. Our collection of heritage properties are near historic Chestertown and are ideal for weddings, family reunions, corporate events and get-aways.
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Comfort Inn & Suites

4. Comfort Inn & Suites

 Chestertown, Maryland
Modern convenience with 81 rooms. Close to Chestertown's Historic District. Breakfast is complimentary.
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Cottage On Kent

5. Cottage On Kent

 Chestertown, Maryland
Cottage On Kent is a charming guest cottage rental. It is located within walking distance to downtown, the Chester River and Washington College.
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Downtown Apartment

6. Downtown Apartment

 Chestertown, Maryland
1 Bedroom Apartment 2 blocks from downtown Chestertown MD on a quiet residential street with one queen size bed.
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Great Oak Manor

7. Great Oak Manor

 Chestertown, Maryland
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Inn at Mitchell House

8. Inn at Mitchell House

 Chestertown, Maryland
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
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Quaint 3-br Downtown House

9. Quaint 3-br Downtown House

 Chestertown, Maryland
3-br, 1-ba short-term rental in downtown Chestertown
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Red Roof Inn & Suites

10. Red Roof Inn & Suites

 Chestertown, Maryland
Modern conveniences with 53 rooms. Close to Chestertown's Historic District.
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River Lodge

11. River Lodge

 Chestertown, Maryland
With its rustic, peaceful waterfront setting, the River Lodge is an excellent venue for a business retreat, private getaway, family reunion, or informal wedding; a four season destination.
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Rolling View Farms, LLC

12. Rolling View Farms, LLC

 Chestertown, Maryland
Please consider staying with us when visiting historic Chestertown. Our five year young Rancher is ideally located within walking distance to Washington College and downtown. This fully equipped home offers the perfect getaway.
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Rolph's Wharf, The River Inn

13. Rolph's Wharf, The River Inn

 Chestertown, Maryland
Spend a night – or a weekend – in charm and comfort. With views of the Chester River and the adjoining farm, the River Inn at Rolph’s Wharf offers you the opportunity to spend a relaxing night or two away from the everyday. Each of the rooms has its
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Safe Harbor Great Oak Landing

14. Safe Harbor Great Oak Landing

 Chestertown, Maryland
28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.
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Stepne Manor

15. Stepne Manor

 Chestertown, Maryland
This historic circa 1690 manor house with wide covered porch is within walking distance to downtown Chestertown. An ideal location for small retreats, meetings and town charm weddings.
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Thornton Estate

16. Thornton Estate

 Chestertown, Maryland
Elegance and seclusion on 300+ acres - Thornton Estate, established in 1664, is a quintessential Eastern Shore estate. The magnificient manor house anchors the 325 acre preserved farm minutes outside of Chestertown, MD.
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White Swan Tavern

17. White Swan Tavern

 Chestertown, Maryland