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Walk to Historic Chestertown: Dog-Friendly Retreat

Chestertown vacation home with kitchen

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

A two-story house with a front porch, a brown door, and a small garden area with potted plants.
A dining area with a wooden table set for four, surrounded by chairs. A white cabinet with a shelf is to the left, and a refrigerator is in the background.
A laundry room with a washer and dryer, a water heater, and a window.
A living room with a brown sofa, a painting on the wall, and a kitchen in the background.
A modern kitchen with white cabinets, stainless steel appliances, and skylights.

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, Chestertown Historic District
    ‪14 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪125 min drive‬

Room options

About the neighborhood

Chestertown

In Chestertown .Within a 10-minute walk of the vacation home, you'll find Washington College and Larrabee Arts Center. Also, River Arts Chestertown is within half a mile (1 km) and Garfield Center for the Arts at the Prince Theater is within 2 miles (3 km).
View more Vacation Homes in ChestertownOpens in a new window

What's nearby

  • Washington College - 3 min walk - 0.2 miles
  • River Arts Chestertown - 11 min walk - 0.6 miles
  • Garfield Center for the Arts at the Prince Theater - 13 min walk - 0.7 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
  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin - ‬2 min drive
  • ‪Royal Farms - ‬4 min drive
  • ‪Procolino's - ‬2 min drive

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
- 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

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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 with cable/satellite channels

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 are welcome
  • Service animals 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property is also known as

552688

Frequently asked questions

How close is Walk to Historic Chestertown: Dog-Friendly Retreat to the airport?

This vacation home is 76.8 mi (106-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

Does Walk to Historic Chestertown: Dog-Friendly Retreat have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Walk to Historic Chestertown: Dog-Friendly Retreat to the beach?

This vacation home is 13 mi (23-min drive) from Betterton Beach and 13.6 mi (25-min drive) from Main Beach. Don't forget your sunscreen!

Does Walk to Historic Chestertown: Dog-Friendly Retreat offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Walk to Historic Chestertown: Dog-Friendly Retreat?

No, there is no casino at this vacation home.

What time is check-in at Walk to Historic Chestertown: Dog-Friendly Retreat?

Check-in begins at 3:00 PM.

Is there free parking at Walk to Historic Chestertown: Dog-Friendly Retreat?

Free parking is not available at this vacation home.

Does Walk to Historic Chestertown: Dog-Friendly Retreat have a pool?

This vacation home does not have a pool.

Does Walk to Historic Chestertown: Dog-Friendly Retreat have a spa?

There are no spa services available at this vacation home.

How close is Walk to Historic Chestertown: Dog-Friendly Retreat to downtown Chestertown?

This vacation home is 0.4 mi away from Chestertown.

Walk to Historic Chestertown: Dog-Friendly Retreat Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Rebecca M.

Liked: Cleanliness, check-in, communication, listing accuracy
Lovely house in great location. Nancy has set the house up perfectly. Highly recommend staying there!
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Carla P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Gary F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Verified review

10/10 Excellent

Susan K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Apr 2026

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