Kent Area Rentals
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
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
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
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
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
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
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
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
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
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
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
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
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
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