Walk to Historic Chestertown: Dog-Friendly Retreat

Top rated by guests
Chestertown Vacation Rental | 2BR | 2BA | 967 Sq Ft | 8 Steps to Enter
Kitchen | Cooking Basics | Dual Coffee Maker | Microwave | Toaster | Blender
Living Room | Board Games | Books
Living area
Kitchen
review stars
10Outstanding
(5 Ratings)
"Lovely house in great location. Nancy has set the house up perfectly. Highly recommend staying there! "
Rebecca M.
Don't miss out! Price and availability may change
10 / 10
Outstanding(5 Ratings)

House in Chestertown, MD

6 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Well priced for this locationPriced under area average

About this house rental

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

INDOOR LIVING
- Smart TV, fireplace
- Dining table
- Walk-in shower, shower/tub combo
- Board games, books
- Ceiling fans in bedrooms

KITCHEN
- Stove/oven, refrigerator, dishwasher
- Cooking basics, dishware/flatware
- Cuisinart dual coffee maker (drip & single-serve pod, coffee provided)
- Microwave, toaster, blender, ice maker
- Limited spices (salt, pepper, garlic salt, paprika, tajin, cinnamon & dill weed)

GENERAL
- Free WiFi
- Central heating & A/C
- Complimentary toiletries, hair dryer
- Washer/dryer, laundry detergent, hangers
- Linens/towels, trash bags/paper towels

FAQ
- Pet fee (paid pre-trip)

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

Amenities at Walk to Historic Chestertown: Dog-Friendly Retreat

Non-smoking
Pets allowed
Family friendly

Map of Chestertown, MD


Ratings and reviews

10 / 10
Outstanding(5 Ratings)
10 / 10Outstanding·Feb 2026
Lovely house in great location. Nancy has set the house up perfectly. Highly recommend staying there!
10 / 10Outstanding·Dec 2025
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!

$$$$
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Walk to Historic Chestertown: Dog-Friendly Retreat. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Walk to Historic Chestertown: Dog-Friendly Retreat pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Walk to Historic Chestertown: Dog-Friendly Retreat?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.