Chester River Rentals
From $542 per night (USD)VRBO
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 $542 per night (USD)VRBO
From $496 per night (USD)VRBO
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern cottage on tranquil large grounds on 20 acres with a pond on one end and a half mile wide creek 800 feet away on ...
From $496 per night (USD)VRBO
From $389 per night (USD)VRBO
Kent Island Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, incl ...
From $389 per night (USD)VRBO
From $882 per night (USD)Expedia
Kent Island Luxury Waterfront
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for ...
From $882 per night (USD)Expedia
From $1336 per night (USD)VRBO
The Colonial Farmhouse with Private Boat Rental
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to the beautiful Eastern Shore of Maryland and relax at the Colonial Farmhouse. This family-friendly, historic pr ...
From $1336 per night (USD)VRBO
From $381 per night (USD)VRBO
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your peaceful riverfront getaway. This home sits directly on the water and is designed for slow mornings, bea ...
From $381 per night (USD)VRBO
From $571 per night (USD)VRBO
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Remodeled in 2023, this light-filled, 2-story private home offers 2,100 sqft of stylish comfort—perfect for a relaxing g ...
From $571 per night (USD)VRBO
From $620 per night (USD)Expedia
Grays Inn Creek Waterfront Pvt Dock Kayaks & View
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 18
Summary: Recently renovated, this spacious home features 7 bedrooms and 5.5 bathrooms, comfortably sleeping 18 guests. ...
From $620 per night (USD)Expedia
From $1380 per night (USD)VRBO
A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 7
Welcome to Lovely Cove Farm. Close to Chestertown and Rock Hall for shopping and dining, but a world away. Secluded and ...
From $1380 per night (USD)VRBO