Chestertown Rentals
From $401 per night (USD)VRBO
Country Estate in Historic District
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. Our house ...
From $401 per night (USD)VRBO
From $329 per night (USD)Expedia
Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic C ...
From $329 per night (USD)Expedia
From $316 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 $316 per night (USD)VRBO
From $498 per night (USD)VRBO
Charming 2-bedroom first floor apartment in Chestertown with Cute Outdoor Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This modern luxury unit boasts a first-floor apartment with two bedrooms, full access to a private back patio/outdoor sp ...
From $498 per night (USD)VRBO
From $619 per night (USD)VRBO
Modern Lux Upstairs apt in Chestertown/Family Friendly/Walk to Shops and Dining!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a s ...
From $619 per night (USD)VRBO
From $1223 per night (USD)Expedia
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 $1223 per night (USD)Expedia
From $171 per night (USD)VRBO
Carriage House Hideaway in Middle of Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens ...
From $171 per night (USD)VRBO
From $298 per night (USD)Expedia
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 $298 per night (USD)Expedia
From $558 per night (USD)VRBO
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This newly renovated historic home leaves nothing to be desired. Between the beautiful decor, amenities, and location th ...
From $558 per night (USD)VRBO
From $1042 per night (USD)VRBO
Spacious luxury home in charming Downtown Chestertown/Pets Welcome/Free Wifi
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a s ...
From $1042 per night (USD)VRBO
From $313 per night (USD)VRBO
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in t ...
From $313 per night (USD)VRBO
From $188 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 $188 per night (USD)Expedia
From $389 per night (USD)VRBO
Historic luxury townhouse in the heart of downtown Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic Luxury Townhouse on High Street – Heart of Downtown Chestertown Welcome to 125 High Street—an exquisitely reno ...
From $389 per night (USD)VRBO
From $456 per night (USD)Expedia
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 $456 per night (USD)Expedia
From $705 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 $705 per night (USD)VRBO
From $159 per night (USD)Expedia
First Floor Studio Apartment in Historic Chestertown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everyt ...
From $159 per night (USD)Expedia
From $515 per night (USD)VRBO
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining ...
From $515 per night (USD)VRBO
From $583 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 $583 per night (USD)VRBO
From $722 per night (USD)VRBO
Down by the River - Charming house on river & walkable to historic Chestertown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Your beautiful retreat in Chestertown awaits! Gorgeous views on the water and walking distance to charming Chestertown. ...
From $722 per night (USD)VRBO
From $527 per night (USD)Expedia
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 $527 per night (USD)Expedia
From $241 per night (USD)VRBO
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
- Bedrooms:
- 2
- 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 $241 per night (USD)VRBO
From $688 per night (USD)Expedia
Pet-Friendly Home on Chester River w/ Dock!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Seasonal Outdoor Pool (May 15-September 15) | Kayaks & Canoe Provided | Crab Traps Calling all waterfront explorers! Lo ...
From $688 per night (USD)Expedia
From $456 per night (USD)VRBO
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recha ...
From $456 per night (USD)VRBO
From $744 per night (USD)VRBO
Breathtaking waterfront home on the Chester River
- Bedrooms:
- 4
- 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 $744 per night (USD)VRBO