Entire home

Walk to Historic Chestertown: Dog-Friendly Retreat

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Photo gallery for Walk to Historic Chestertown: Dog-Friendly Retreat

Exterior
Dining
TV, fireplace, books
Interior
Fridge, microwave, stovetop, dishwasher

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms967 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Chestertown, MD
  • Place, Washington College
    ‪3 min walk‬
  • Place, River Arts Chestertown
    ‪11 min walk‬
  • Place, Wilmer Park
    ‪14 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪106 min drive‬

Room options

Similar properties

About the neighborhood

Chestertown

With a stay at this vacation home in Chestertown, you'll be a 3-minute walk from Washington College and 9 minutes by foot from Larrabee Arts Center. .This vacation home is 0.6 mi (0.9 km) from Garfield Center for the Arts at the Prince Theater and 0.6 mi (1 km) from River Arts Chestertown.

What's nearby

  • Washington College - 3 min walk - 0.2 miles
  • River Arts Chestertown - 11 min walk - 0.6 miles
  • Wilmer Park - 14 min walk - 0.8 miles
  • Historical Society of Kent County Maryland - 14 min walk - 0.8 miles
  • Chestertown Historic District - 14 min walk - 0.8 miles

Getting around

  • Baltimore, MD (MTN-Martin State) - 106 min drive

Restaurants

  • ‪Milano's Pizzeria - ‬4 min drive
  • ‪Royal Farms - ‬4 min drive
  • ‪Dunkin - ‬2 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Royal Farms - ‬12 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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

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
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace. There's a private patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Conveniences include a coffee/tea maker and a washing machine.
Take in the views from a garden and make use of amenities such as barbecue grills.
Guests will find features like internet access and onsite parking.

Property amenities

Internet

  • Available in the house: Internet access

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Books
  • Games
  • TV

Outdoor areas

  • Barbecue grill
  • Garden
  • Patio

Laundry

  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Unit size: 967 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 18

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Note from host: A maximum of 2 pets are allowed.

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

552688

Walk to Historic Chestertown: Dog-Friendly Retreat Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Rebecca M.

Liked: Cleanliness
Lovely house in great location. Nancy has set the house up perfectly. Highly recommend staying there!
Stayed 3 nights in Jan 2026

10/10 Excellent

Gary F.

Liked: Cleanliness
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!
Stayed 3 nights in Dec 2025