10/10 Excellent
Robin G.
15 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Robin G.
Stayed 2 nights in Jun 2025
Entire home
Country Estate in Historic District
Family-friendly holiday home in Chestertown
Photo gallery for Country Estate in Historic District
Reviews
10 out of 10
Exceptional
5 bedrooms3+ bathroomsSleeps 10
Popular amenities
Explore the area
Chestertown, MD
- Place, River Arts Chestertown5 min walk
- Place, Historical Society of Kent County Maryland8 min walk
- Place, Washington College8 min walk
- Airport, Easton, MD (ESN-Easton - Newnam)58 min drive
Rooms & beds
5 bedrooms (sleeps 10)
2
1 Queen Bed
First floor master suite
1 Queen Bed
Loft
2 Single Beds
Master
1 King Bed
Second story bedroom
1 Queen Bed
3 bathrooms, 1 half bathroom
First floor en suite bath
Toilet · Shower only
First floor powder room
Toilet
Second floor bath/laundry room
Toilet
Second floor master bath
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
About this property
Country Estate in Historic District
Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath.
Our house is in the historic district of Chestertown, and a two block walk from both Washington College and the Chestertown waterfront. It features two master bedroom suites, one on the ground floor. There are three more bedrooms and a secluded yard. Just outside your garden gate is over an acre of manicured gardens to explore. Gas grill on patio
Over the years, we have stayed in a lot of vacation rentals, and we know what we need as guests.
1. Comfortable beds and furniture
2. Quality linens and towels
3. Limitless hot water
4. Well-equipped kitchen (hate buying
corkscrews!)
5. Peace and privacy, but security in knowing
someone is always available.
6. CLEAN, CLEAN, CLEAN.
Our goal is to give you the experience we would want to have. To maintain quality control we do our own cleaning, and we are available 24/7 if you should need anything, but will be invisible otherwise.
The entire house and fenced yard is yours, as well as the large gardens, which are right outside the back gate. We might be doing some gardening in the large garden, but will keep our distance.
Our house is in the historic district of Chestertown, and a two block walk from both Washington College and the Chestertown waterfront. It features two master bedroom suites, one on the ground floor. There are three more bedrooms and a secluded yard. Just outside your garden gate is over an acre of manicured gardens to explore. Gas grill on patio
Over the years, we have stayed in a lot of vacation rentals, and we know what we need as guests.
1. Comfortable beds and furniture
2. Quality linens and towels
3. Limitless hot water
4. Well-equipped kitchen (hate buying
corkscrews!)
5. Peace and privacy, but security in knowing
someone is always available.
6. CLEAN, CLEAN, CLEAN.
Our goal is to give you the experience we would want to have. To maintain quality control we do our own cleaning, and we are available 24/7 if you should need anything, but will be invisible otherwise.
The entire house and fenced yard is yours, as well as the large gardens, which are right outside the back gate. We might be doing some gardening in the large garden, but will keep our distance.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
No parties.
Pets
Pets allowed
One time $20 pet fee
Smoking
Smoking is not permitted
No smoking on property.
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
On-site parties or group events are strictly prohibited
Note from host: No parties.
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Chestertown
Located in Chestertown, this holiday home is in the city centre. Chestertown Historic District and Wilmer Park reflect the area's natural beauty and area attractions include Crumpton Auction and Hazel Miner Monument.
Chestertown, MD
What's nearby
- River Arts Chestertown - 5 min walk - 0.4 km
- Historical Society of Kent County Maryland - 8 min walk - 0.7 km
- Washington College - 8 min walk - 0.7 km
- Wilmer Park - 9 min walk - 0.8 km
- Rolphs Wharf Marina - 12 min drive - 9.4 km
Getting around
Restaurants
- McDonald's - 3 min drive
- Royal Farms - 5 min walk
- Dunkin - 2 min drive
- Procolino's - 3 min drive
- Subway - 18 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
Gwen R.
11 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Gwen R.
Stayed 2 nights in May 2025
10/10 Excellent
Elder p.
4 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wedding Weekend
Elder p.
Stayed 2 nights in May 2025
10/10 Excellent
Chris W.
15 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
Chris W.
Stayed 2 nights in Oct 2023
10/10 Excellent
David K.
16 Dec 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best place ever
David K.
Stayed 2 nights in Dec 2023
10/10 Excellent
Kathleen S.
6 Aug 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great town, great place to stay
Kathleen S.
Stayed 5 nights in Jul 2022
10/10 Excellent
ira d.
6 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
anniversary get away
ira d.
Stayed 2 nights in Jul 2024
10/10 Excellent
Susan N.
30 Jan 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
walking distance to downtown and historic Chestertown and campus. well located.
Susan N.
Stayed 2 nights in Jan 2023
10/10 Excellent
Stephen C.
11 Nov 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent
Stephen C.
Stayed 2 nights in Nov 2023
10/10 Excellent
Michael D.
2 Mar 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chestertown wedding
Michael D.
Stayed 3 nights in Feb 2024
10/10 Excellent
Christina c.
25 Sept 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely gorgeous
Christina c.
Stayed 2 nights in Sep 2022
10/10 Excellent
sue B.
12 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Welcome
sue B.
Stayed 7 nights in Apr 2023
10/10 Excellent
susan s.
10 Dec 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and amazing house
susan s.
Stayed 2 nights in Dec 2023
10/10 Excellent
Margaret H., Ocean View, DE
31 Oct 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay in Chestertown
Margaret H.
Stayed 3 nights in Oct 2022
10/10 Excellent
Len L.
26 Nov 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
The best place!
Len L.
Stayed 4 nights in Nov 2023
10/10 Excellent
Richard L.
13 Dec 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Outstanding
Richard L.
Stayed 2 nights in Dec 2022
10/10 Excellent
Diana M.
20 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
WHAT A JEWEL
Diana M.
Stayed 3 nights in Oct 2024
10/10 Excellent
Deborah K.
26 Aug 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property in middle of Chestertown
Deborah K.
Stayed 2 nights in Aug 2023
10/10 Excellent
Mary Beth K.
21 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spectacular property
Mary Beth K.
Stayed 5 nights in Apr 2023
10/10 Excellent
Dmitry K.
3 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Property
Dmitry K.
Stayed 3 nights in Sep 2023
10/10 Excellent
Mary S., Alexandria, Virginia
1 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous historic home; perfect location
Mary S.
Stayed 3 nights in Mar 2023
10/10 Excellent
Sondra W.
5 Nov 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
November 2023
Sondra W.
Stayed 2 nights in Nov 2023
10/10 Excellent
Mary K.
23 Oct 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful!!
Mary K.
Stayed 3 nights in Oct 2022
10/10 Excellent
Dominick B.
27 Aug 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house and property!
Dominick B.
Stayed 1 night in Aug 2020
10/10 Excellent
Amy D., Collegeville, PA, USA
31 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chestertown Fun
Amy D.
Stayed 8 nights in Jul 2023
About the host
Hosted by Robert Kestell
Languages:
Spanish, Portuguese
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