House
5

Walk to Historic Chestertown: Dog-Friendly Retreat

Property ID: 552688ChestertownMDUS
Sleeps 62 BR2 BA
Book with confidence

Most trips qualify for free 48 hour cancellation. Add dates for more information.

Description

Fenced Backyard | Furnished Deck | Family Game Nights

Step into a storybook at 'Sage Bungalow' in Chestertown, where historic streets and riverside breezes set the scene for adventure. Head downtown to explore local art galleries, enjoy a picnic in the leafy serenity of Wilmer Park, or glide along the Chester River on a boat cruise. After a fun day, retreat to the 2-bed, 2-bath home to cozy up by the fire or settle in for a night of board games. Your Eastern Shore escape awaits!

Amenities

  • Pets Allowed
  • Kitchen
  • Essentials
  • Free Parking
  • Deck
  • Central Heating
  • Central Air Conditioning
  • Wireless Internet (WIFI)
  • Washer

Map

Location Details

- 0.3 miles to Washington College

- 0.5 miles to Historical Society of Kent County

- 0.7 miles to Chestertown Historic District: Chestertown Farmers Market (every Saturday from 8:00 AM to 12:00 PM), Chestertown Tea Party Festival (Memorial Day weekend), parks, restaurants, art galleries, shops

- 1 mile to Chester River

- 18 miles to Eastern Neck National Wildlife Refuge

- 67 miles to Baltimore/Washington International Airport

Reviews

5
1 review
  • 5/5

    Highly recommend if you're staying in Chestertown. Everything is near by and the comforts and quality of stay are above the five star review. Comfortable and warm home with all the amenities. Just bring some personable items and your set. Fairly priced too! Definitely would stay again.Thank you!

    *This review was originally posted on Vrbo

    Gary
    Published January 9, 2026
    Manager's Response:

    Thank you for taking the time to share your experience during you recent stay. I'm glad that you found Sage Bungalow to be comfortable for you and your family. Please keep us in mind for your next visit to Chestertown. Nancy

  • 1

Still have questions?

Reach out help with general questions about the property.

We make vacation rental easy

Our modern approach to hospitality and property management puts the focus on five-star stays and owner-centric strategies.
Guests rest easy

Guests rest easy

Count on the best rates, flexible cancellations, and vetted homes

Owners get support

Owners get support

Reach your rental goals with expert guidance and exclusive tools

Everyone benefits

Everyone benefits

Trust our team for excellent service and best-in-class support

Add dates for prices
5
1 reviews

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Guests
Select Guests
  • This property has a maximum occupancy of 6 guests, not including infants.
  • Pets are allowed at this property.
Adults
0
Children
Ages 2-12
0
Infants
0
Pets