Chestertown Rentals
From $409 per night (USD)VRBO
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)VRBO
From $500 per night (USD)Expedia
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)Expedia
From $368 per night (USD)VRBO
Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Discover this lovely 2 bedroom and loft gem in Chestertown. This welcoming apartment features 3 queen beds, perfect for ...
From $368 per night (USD)VRBO
From $336 per night (USD)Expedia
Walk to Historic Chestertown: Dog-Friendly Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fenced Backyard | Furnished Deck | Family Game Nights Step into a storybook at 'Sage Bungalow' in Chestertown, where hi ...
From $336 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 $281 per night (USD)Expedia
Secluded Cottage in Middle of Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens ...
From $281 per night (USD)Expedia
From $352 per night (USD)VRBO
Newly restored apartment in the heart of Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of al ...
From $352 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
From $642 per night (USD)VRBO
Victorian Hideaway: Beautiful Exterior, Modern interior
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet ...
From $642 per night (USD)VRBO