Walk to Historic Chestertown: Dog-Friendly Retreat

Chestertown, Maryland
$254 avg/night
Bed 2

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

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

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 967 Sq Ft (90 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Internet Access
  • OUTDOORS

    Barbecue Grill Garden Patio
  • BATHROOMS

    2 Bathrooms Hair Dryer Towels Provided
  • LANGS SPOKEN

    English French German Spanish
  • ENTERTAINMENT

    Books Games TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Rebecca M.

    Submitted Feb 11, 2026

    Stayed Jan 16, 2026

    Lovely house in great location. Nancy has set the house up perfectly. Highly recommend staying there!

  • Gary F.

    Submitted Dec 26, 2025

    Stayed Dec 22, 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!

Your dates are Available!

Total

Includes taxes and fees
$254+
View details