5 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

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7 Vacation rentals

(2) Very Good 

11

Vacation home in Chestertown

Maryland / Chestertown

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or …see more

from $145 / night

$940 - $1150 / week

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from $145 / night

(3) Excellent 

28

Vacation home in Chestertown

Maryland / Chestertown

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Quaint, modest one-bedroom cottage near the Chesapeake Bay. Relax and discover the culture, history, nature & cuisine of Maryland's Eastern Shore. Perfect for families, couples and friends. Guests can enjoy great views of the bay and sunsets from the owner's property, w …see more

from $120 / night

$650 - $850 / week

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from $120 / night

(3) Very Good 

14

Home rental in Chestertown

Maryland / Chestertown

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venu …see more

from $295 / night

$1995 / week

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from $295 / night

(7) Excellent 

10

Chestertown Vacation apartment rental

Maryland / Chestertown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 24 mi
  • Child friendly
  • Air conditioning
This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An outdoor deck with cafe table and chairs is a nice place to sit on a sunn …see more

from $99 / night

$685 / week

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from $99 / night

(1) Excellent 

16

Chestertown Vacation home rental

Maryland / Chestertown

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This gorgeous home is located directly on the Chester River in Chestertown, Md, on the Eastern shore. There are 5 bedrooms, one down and four on the second floor. On the main floor there is a great room that is part kitchen, part TV area and part dining room. Off of th …see more

from $650 / night

$4000 / week

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from $650 / night

(1) Excellent 

7

Vacation apartment in Chestertown

Maryland / Chestertown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 2 guests. It is the perfect place for enjoying this historic, artistic town on Maryland's Eastern Shore. The space includes kitchen/liv …see more

from $88 / night

$600 / week

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from $88 / night

(1) Excellent 

22

Vacation home in Chestertown

Maryland / Chestertown

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from house and wraparound deck. Perfect destination for a couples getaway, family trip or friends gathering to enjoy the Bay & Sunsets. Located in the scenic, serene environs of the Eastern S …see more

from $145 / night

$900 - $1100 / week

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from $145 / night

1