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Kent Area Rentals

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Results: 114 Rentals

  • Breathtaking waterfront home on the Chester River
    From $775 per night (USD)

    VRBO

    Breathtaking waterfront home on the Chester River

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated ent ...

    From $775 per night (USD)

    VRBO

    Details
  • Waterfront w\/Deepwater Pier Walking Distance to Downtown Chestertown
    From $506 per night (USD)

    Expedia

    Waterfront w\/Deepwater Pier Walking Distance to Downtown Chestertown

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened ...

    From $506 per night (USD)

    Expedia

    Details
  • Charming  Chestertown Waterfront Cottage
    From $243 per night (USD)

    VRBO

    Charming Chestertown Waterfront Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy your stay in Chestertown in a waterfront home on a tidal creek that is only minutes from historic downtown and Was ...

    From $243 per night (USD)

    VRBO

    Details
  • Eastern Shore Get Away
    From $125 per night (USD)

    VRBO

    Eastern Shore Get Away

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Located on Maryland's Eastern Shore, on the Chester River, this fully furnished 1 bedroom, 1 bathroom apartment has all ...

    From $125 per night (USD)

    VRBO

    Details
  • 5 bedroom Historic Victorian by Chester River
    From $299 per night (USD)

    VRBO

    5 bedroom Historic Victorian by Chester River

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Built in1914 this historic Victorian offers huge wrap around porch. Hardwood floors, vintage Heartland Stove, Antiques, ...

    From $299 per night (USD)

    VRBO

    Details
  • Beautiful Waterfront Estate
    From $2520 per night (USD)

    VRBO

    Beautiful Waterfront Estate

    Bedrooms:
    9
    Bathrooms:
    11
    Sleeps:
    30

    Brittland Manor was built in 1938 and sits on 530 riverside acres. When you drive up the long curved lane you are surro ...

    From $2520 per night (USD)

    VRBO

    Details
  • Private Waterfront Paradise w\/ Pier - Kayak to Historic Chestertown!
    From $450 per night (USD)

    VRBO

    Private Waterfront Paradise w\/ Pier - Kayak to Historic Chestertown!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire t ...

    From $450 per night (USD)

    VRBO

    Details
  • Harbor View Haven | Waterfront w\/ Dock + HOT TUB!
    From $527 per night (USD)

    Expedia

    Harbor View Haven | Waterfront w\/ Dock + HOT TUB!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    BNB Breeze Presents Harbor View Haven! This exquisite waterfront property offers a captivating retreat to relax and rec ...

    From $527 per night (USD)

    Expedia

    Details
  • Lovely, Recently-Renovated Home in Chestertown which sleeps 7.
    From $199 per night (USD)

    VRBO

    Lovely, Recently-Renovated Home in Chestertown which sleeps 7.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    “Old Bridge” is a 100-year-old house in a quiet Kingstown section of Chestertown. The house is an "American Four Square" ...

    From $199 per night (USD)

    VRBO

    Details
  • Waterfront Millington Vacation Rental w\/ Hot Tub!
    From $406 per night (USD)

    Expedia

    Waterfront Millington Vacation Rental w\/ Hot Tub!

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    10

    Book a tranquil East Coast getaway at this 60-acre vacation rental in Millington, MD. This secluded waterfront property ...

    From $406 per night (USD)

    Expedia

    Details
  • Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
    From $400 per night (USD)

    VRBO

    Waterfront venue on secluded 60 acres with 2 homes great for a family retreat

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    8

    Relax with the whole family at this peaceful secluded property. Located on the Chester River in Millington, MD, Pine For ...

    From $400 per night (USD)

    VRBO

    Details
  • Private pier and pool at this waterfront Chestertown home
    From $711 per night (USD)

    Expedia

    Private pier and pool at this waterfront Chestertown home

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    This private waterfront river home in beautiful historic Chestertown has its own private pier and pool - all on a quiet ...

    From $711 per night (USD)

    Expedia

    Details
  • The Lazy River House
    From $550 per night (USD)

    VRBO

    The Lazy River House

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to this freshly renovated, waterfront home on the Chester River. Gorgeous sunsets, picturesque views of the Rive ...

    From $550 per night (USD)

    VRBO

    Details
  • River Lodge, Casual Riverfront setting
    From $619 per night (USD)

    VRBO

    River Lodge, Casual Riverfront setting

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    The River Lodge sits on the scenic Chester River located 5 miles outside of Chestertown. It's the perfect little get ...

    From $619 per night (USD)

    VRBO

    Details