Chestertown Vacation Home Rentals(10)
Adorable, Fully Remodeled, Heart of Quaint Historic District
- 2 Bedrooms, Sleeps 4
$135 -
$175
per night
2 night Minimum Stay
- 2 BR,
- Sleeps 4
Historic House, Steps to Shopping, Dining and Chester River
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Waterfront Farm with Pool, Private Dock and Kayaks
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 8
$500
per night
2 night Minimum Stay
- 4 BR,
- 4 BA,
- Sleeps 8
Mill Creek House
- 2 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 4
$200
per night
2 night Minimum Stay
- 2 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 4
Chester River House with Views
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 7
$130 -
$180
per night
2 night Minimum Stay
- 3 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 7
Chester River Waterfront, Magnificent Views, Dock, Beach
- 2 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$300 -
$350
per night
2 night Minimum Stay
- 2 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Historic in-Town House/Historic District of Chestertown ~MD~
- 3 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 7
$300 -
$400
per night
2 night Minimum Stay
- 3 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 7
Exquisite Water-Front Chesapeake Bay Home Near Chestertown, Md
- 3 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
- 3 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Running Fox, a Historic Country Retreat
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 9
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
Historic Stepne Manor on Maryland's Eastern Shore
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 15
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 15
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