Vacation Rentals by Owner

Chestertown Vacation Rentals Show this location only Back to top

•   Waterfront, Stylish, Historic Retreat 2BR/2BA – Sleeps 3-4 – Chestertown #328116
  7
  $220 - $240 per night 2 night min stay

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•   Waterfront Farm with Pool, Private Dock and Kayaks 4BR/4BA – Sleeps 8 – Chestertown #410328
  6
  $500 per night 2 night min stay

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•   Exquisite Water-Front Chesapeake Bay Home Near Chestertown, Md 3BR+/3.5BA – Sleeps 8-10 – Chestertown #352199
  1
  From $595/nIGHT

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•   Water Front Retreat - Sunrise and Sunset Water Views 3BR/3BA – Sleeps 5-8 – Chestertown #294688
  11
  $300 - $350 per night 2 night min stay

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•   Still Pond Creek Waterfont Estate W/ Beach, Privacy and Dock! 4BR+/4.5BA – Sleeps 10-13 – Chestertown #356548
  15
  From $350/nt or $1,750 to $3,000/wk

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•   Historic House, Steps to Shopping, Dining and Chester River 3BR+/2.5BA – Sleeps 6-8 – Chestertown #389952
  3
  From $2000/wk or $300-$350/nt

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•   Historic in-Town House/Historic District of Chestertown MD 3BR/4.5BA – Sleeps 5-7 – Chestertown #228431
  15
  $300 - $400 per night 2 night min stay

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•   Brittland Manor 11BR+/8.5BA – Sleeps 26 – Chestertown #223074
  0
  $5995/wknd - $9995/wk

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•   Running Fox, a Historic Country Retreat 4BR+/2.5BA – Sleeps 9 – Chestertown #213261
  0
  $1050/wknd - $3500/wk

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•   River Lodge 4BR+/2BA – Sleeps 10-12 – Chestertown #219567
  0
  $1050/wknd - $3500/wk

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•   Waterfront 3 BR Cute Country Cottage.Deep Water,Dock, 2 Mi from Town 3BR/1BA – Sleeps 6 – Chestertown #418738
  7
  $200 - $250 per night 2 night min stay

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•   Chester River House with Views 3BR/1.5BA – Sleeps 7 – Chestertown #429782
  6
  $130 - $180 per night 2 night min stay

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•   Adorable, Fully Remodeled, Heart of Quaint Historic District 2BR/1.5BA – Sleeps 4 – Chestertown #327701
  2
  $135 - $175 per night 2 night min stay

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•   Chester River Waterfront, Magnificent Views, Dock, Beach 2BR+/1.5BA – Sleeps 6 – Chestertown #431733
  1
  $300 - $350 per night 2 night min stay

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•   Mill Creek House 2BR/1.5BA – Sleeps 4 – Chestertown #473897
  0
  $200 per night 2 night min stay

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•   Historic Stepne Manor on Maryland's Eastern Shore 5BR/3.5BA – Sleeps 15 – Chestertown #124956
  1
  From $1550/wknd - $3850/wk

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•   Escape to Kent Fields Farm a Country Estate for All Seasons. 4BR+/4.5BA – Sleeps 8-12 – Chestertown #355727
  0
  $2500.00- $3,500.00/wk $450-$650/nt +tax

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