Chestertown Rentals
From $500 per night (USD)VRBO
Wren Retweet- Country Estate in Center of C’Town
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
History with modern convenience, including first floor bedroom with private bath and super fast internet. Our house is ...
From $500 per night (USD)VRBO
From $409 per night (USD)Expedia
Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful 1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic ...
From $409 per night (USD)Expedia
From $1659 per night (USD)VRBO
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best ...
From $1659 per night (USD)VRBO
From $220 per night (USD)Expedia
Historic Downtown Garden Oasis with Private Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesth ...
From $220 per night (USD)Expedia
From $545 per night (USD)VRBO
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. W ...
From $545 per night (USD)VRBO