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Walk to Historic Chestertown: Dog-Friendly Retreat

Entire home in Chestertown, MD

6 guests·2 bedrooms·2 bathrooms
5.0 · 17 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Fenced backyard and deck provide private dog-friendly outdoor gatherings.

Location & Accessibility

Location & Accessibility

Walkable to downtown shops, galleries, and riverside boat cruises.

Value & Savings

Value & Savings

Guests save an average of 17% when booking this stay vs. Airbnb and Vrbo.

Property details

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 space
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)

Guest access
Guests will have access to the entire property

Other things to note
- 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

Sleeping arrangements

Bedroom 1

1 king Bed

Bedroom 2

1 queen Bed

Living room

1 sofa Bed

What’s included

  • Free parking on premises

    Free parking on premises

  • EV charger

    EV charger

  • Washer

    Washer

  • Dryer

    Dryer

  • Central air conditioning

    Central air conditioning

  • Central heating

    Central heating

  • Indoor fireplace

    Indoor fireplace

  • Pets allowed

    Pets allowed

Guest reviews

Star icon 5.0 | 17 reviews
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4
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A

Ana

Star Icon 0 0Star Icon 0 1Star Icon 0 2Star Icon 0 3Star Icon 0 4

August 2026

The home was lovely and very well kept and stocked with many necessities. Perfect if you’re traveling with dogs. Mine loved the yard.

K

Krissy

Star Icon 1 0Star Icon 1 1Star Icon 1 2Star Icon 1 3Star Icon 1 4

July 2026

This bungalow was perfect for our stay in Chestertown. It was easy to get to everything within Chestertown and Rock Hall. The host definitely made sure you have everything if you forgot something. Thank you for the amazing place!

R

Rebecca

Star Icon 2 0Star Icon 2 1Star Icon 2 2Star Icon 2 3Star Icon 2 4

July 2026

Really nice cottage well equipped. Great AC was important in 100 degree weather. Too hot to enjoy the deck but my dog likes the securely fenced back yard as well as a nearby walking trail. The street out from was rather busy but in was quiet inside.

A

Angela

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June 2026

Very clean and comfortable. Excellent sleep!

Know before you go

House rules

Check-in: 3:00pm

Checkout: 11:00am

Pets allowed

Min. age to rent: 18

No smoking

No parties

Have a question about this property?

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