5 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

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21 Vacation rentals

(7) Excellent 

10

Chestertown Vacation apartment rental

Maryland / Chestertown

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • 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 $89 / night

$685 / week

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avg. 2 hours 53 minutes

from $89 / night

(3) 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 - $1,150 / week

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from $145 / 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

$1,995 / week

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from $295 / night

(2) Very Good 

16

Chestertown Vacation home rental

Maryland / Chestertown

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 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

$4,000 / week

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from $650 / night

(1) Excellent 

22

Vacation home in Chestertown

Maryland / Chestertown

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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 $115 / night

$500 - $900 / week

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Responds fast!
avg. 2 hours 53 minutes

from $115 / night

(3) Excellent 

25

Vacation home with swimming pool in Chestertown

Maryland / Chestertown

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
Lovely home in a quiet setting very comfortably furnished all you need for a relaxing getaway. Located 7 miles from the center of Chestertown & 5 miles from the center of Rock Hall. This spacious rancher offers four bedrooms two of the four are master suite's, 3 bathroo …see more

from $200 / night

$1,100 - $2,000 / week

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from $200 / 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

$450 / week

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Responds fast!
avg. 2 hours 53 minutes

from $88 / night

(2) Excellent 

17

Chestertown Vacation home rental

Maryland / Chestertown

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Nestled behind the main house with a fenced garden, the cottage is a cozy respite after a busy day site seeing or visiting with local friends. Relax and discover the culture, history, nature, and cuisines of Maryland's Eastern Shore. Perfect for folks traveling with a d …see more

from $135 / night

$800 / week

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from $135 / night