Walk to Historic Chestertown: Dog-Friendly Retreat

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 deck with a round metal table and chairs, a red umbrella, and a green grill.
A house with a wooden deck, a red umbrella, and a staircase leading to a porch.
A living room with a fireplace, a television mounted above it, and a large painting on the wall.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove. There are skylights above the kitchen, and a dining area with a table and chairs is visible.

Reviews

10 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Near Washington College

Popular amenities

  • Patio
  • Barbecue
  • Air-conditioning
  • Pet-friendly
  • Refrigerator
  • Onsite parking available

Explore the area

View 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)
    ‪126 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Additional Sleeping (Living Room)

1 Double Sofa Bed

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Full Bathroom

Full Bathroom

Spaces

Deck or patio
Kitchen
Garden

Add dates for prices

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About the area

Chestertown

Chestertown is home to this holiday home. Chesapeake Bay and Chestertown Historic District reflect the area's natural beauty and area attractions include Larrabee Arts Center and Garfield Center for the Arts at the Prince Theater. Schooner Sultana and Crumpton Auction are also worth visiting.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Washington College - 3 min walk - 0.3 km
  • River Arts Chestertown - 11 min walk - 1.0 km
  • Historical Society of Kent County Maryland - 14 min walk - 1.2 km
  • Chestertown Historic District - 14 min walk - 1.2 km
  • Sumner Hall - 16 min walk - 1.3 km

Getting around

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

Restaurants

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

Frequently asked questions

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

Yes, pets are allowed at this property.

How much does it cost to stay at Walk to Historic Chestertown: Dog-Friendly Retreat?

As of 7 Nov 2026, prices found for a 1-night stay for 2 adults at Walk to Historic Chestertown: Dog-Friendly Retreat on 18 Jan 2027 start from AU$1,171, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Walk to Historic Chestertown: Dog-Friendly Retreat?

On-site parking is available at the property.

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

Check-in begins at 3:00 PM.

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

Checkout is at 11:00 AM.

Where is Walk to Historic Chestertown: Dog-Friendly Retreat located?

Situated in Chestertown, this holiday home is within a 10-minute walk of Washington College and Larrabee Arts Center. River Arts Chestertown and Chestertown Farmers Market are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 11 out of 11 reviews
Rating 8 - Good. 0 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely stay! It is a perfect location and a well kept and well stocked home. Every detail was so thoughtful. We would stay again!
Stayed 4 nights in Sep 2026
Response from VrboOwner on 16 Oct 2026
Thank you so much for taking the time to leave your review. I'm so glad that you enjoyed your stay! I'd love to welcome you back to Sage Bungalow again. - Nancy
Verified review

10/10 Excellent

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

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely home, we felt quite welcome. Pleasantly surprised with all the amenities. Clean, comfortable. Lovely little town. We will plan on returning.
Stayed 7 nights in Aug 2026
Response from VrboOwner on 20 Sept 2026
Thank you for taking the time to leave a review. We're so glad you felt welcome and enjoyed the amenities, cleanliness, and comfort of the home, as well as exploring the charm of the town. Please do visit us again. - Nancy
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home is immaculate. The beds are comfortable. Kitchen well equipped. Great location to walk downtown. Host available for any needs. Absolutely great stay!!
Stayed 3 nights in Aug 2026
Response from VrboOwner on 5 Sept 2026
Thank you for the wonderful feedback! We're so glad that you found the home comfortable, and that the kitchen had everything you needed. It means a lot to hear you had such a great stay! - Nancy
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was perfect! Within walking distance to shopping and dining. Clean and comfortable. Kitchen well stocked, toiletries perfect, beds comfortable. Host was available for any issues if needed but fortunately there were none. Looking forward to our next stay!
Stayed 3 nights in Jul 2026
Response from VrboOwner on 2 Aug 2026
Thank you for taking the time to leave your thorough review. Looking forward to hosting you again! - Nancy
Verified review

10/10 Excellent

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
Response from VrboOwner on 5 May 2026
Thank you for taking the time to leave your review. I'm glad that you and your family (including your pup) enjoyed your stay. Please stay with us again! - Nancy
Verified review

10/10 Excellent

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
Response from VrboOwner on 9 Jan 2026
Thank you for taking the time to share your experience during you recent stay. I'm glad that you found Sage Bungalow to be comfortable for you and your family. Please keep us in mind for your next visit to Chestertown. Nancy
Verified review

10/10 Excellent

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
Response from VrboOwner on 11 May 2026
Thank you for taking the time to leave a review. I'm glad that you enjoyed your stay and the back deck. Please do stay with us again. - Nancy
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a great location. Loved walking downtown to Farmers market on Saturday. Clean and beautiful small house. Had everything and more than we needed. Enjoyed to back deck every day. Love handicap accessible shower with rails and seat. Well thought out home. Many thanks
Stayed 3 nights in May 2026
Response from VrboOwner on 18 June 2026
Thank you for taking the time to leave your thorough review. I'm glad to hear that you were able to enjoy the back deck as well a walk to the farmer's market. Those are some of the things I enjoy there too. Welcome back anytime! - Nancy
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 2 nights in Sep 2026
Response from Walk to Historic Chestertown: Dog-Friendly Retreat on 27 Oct 2026
Thanks for sharing your experience. - Nancy
Verified review

10/10 Excellent

Stayed 4 nights in Jun 2026
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