Walk to Historic Chestertown: Dog-Friendly Retreat
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!
-- THE PROPERTY --
SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Living Room: 1 queen sleeper sofa
OUTDOOR LIVING - Deck w/ dining space & charcoal grill - Covered porch w/ 2 chairs - Fenced backyard
ACCESSIBILITY - Single-story home, 8 steps to enter
PARKING - Driveway (1 vehicle) - EV outlet (bring your own charging cable)
-- THE LOCATION --
- 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
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking - Pet friendly w/ $50 fee (+ fees & taxes, dogs only, 2 max) - No events, parties, or large gatherings - Must be at least 18 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in
ADDITIONAL INFORMATION - This single-story home requires 8 steps to enter
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Chestertown
Chestertown is home to this holiday home. Chesapeake Bay and Chestertown Historic District reflect the area's natural beauty and area attractions include Larrabee Arts Center and Garfield Center for the Arts at the Prince Theater. Crumpton Auction and The Mainstay are also worth visiting.
Garfield Center for the Arts at the Prince Theater - 13 min walk - 1.1 km
Historical Society of Kent County Maryland - 14 min walk - 1.2 km
Chestertown Historic District - 14 min walk - 1.2 km
Getting around
Baltimore, MD (MTN-Martin State) - 106 min drive
Restaurants
Milano's Pizzeria - 4 min drive
McDonald's - 3 min drive
Dunkin - 2 min drive
Royal Farms - 4 min drive
Procolino's - 2 min drive
Frequently asked questions
Is Walk to Historic Chestertown: Dog-Friendly Retreat pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Walk to Historic Chestertown: Dog-Friendly Retreat?
As of 10 May 2026, prices found for a 1-night stay for 2 adults at Walk to Historic Chestertown: Dog-Friendly Retreat on 21 June 2026 start from AU$375, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Walk to Historic Chestertown: Dog-Friendly Retreat?
On-site parking is available at the property.
What time is check-in at Walk to Historic Chestertown: Dog-Friendly Retreat?
Check-in begins at 3:00 PM.
What time is check-out at Walk to Historic Chestertown: Dog-Friendly Retreat?
Checkout is at 11:00 AM.
Where is Walk to Historic Chestertown: Dog-Friendly Retreat located?
Situated in Chestertown, this holiday home is within a 10-minute walk of Washington College and Larrabee Arts Center. River Arts Chestertown and Garfield Center for the Arts at the Prince Theater are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We had a very nice stay at property, beds comfortable,well stocked kitchen. The house well thought out and great for your pup. Thank you.
Carla P.
Stayed 3 nights in Apr 2026
Response from VrboOwner on 5 May 2026
Thank you for taking the time to leave your review. I'm glad that you and your family (including your pup) enjoyed your stay. Please stay with us again! - Nancy
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!
Gary F.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 9 Jan 2026
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
The house was in excellent condition. Everything seemed quite new. And we appreciated how well it was equipped -- the kitchen, bathrooms and bedrooms. We did not end up cooking any meals because of our short stay, but did make use of the coffee maker and fridge. And we enjoyed the back deck too!