Top-rated for comfort — guests feel right at home here.
Balcony
A rare find - enjoy views from the balcony.
5 bedrooms4 bathroomsSleeps 10
Popular amenities
Balcony or patio
Barbecue grill
Free WiFi
Kitchen
Pet-friendly
Air conditioning
Explore the area
Chestertown, MD
River Arts Chestertown
Place, River Arts Chestertown
5 min walk
Washington College
Place, Washington College
8 min walk
Chestertown Historic District
Place, Chestertown Historic District
8 min walk
Baltimore, MD (MTN-Martin State)
Airport, Baltimore, MD (MTN-Martin State)
126 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Loft
+2
1 King Bed, 3 Queen Beds and 2 Twin Beds
4 bathrooms
Bathroom
Toilet
First floor en suite bath
Toilet · Shower only
Second floor bath/laundry room
Toilet
Second floor master bath
Spaces
Deck or patio
Kitchen
Balcony
Separate dining area
Number of living rooms
Garden
About this property
Wren Retweet- Country Estate in Center of C’Town
History with modern convenience, including first floor bedroom with private bath and super fast internet.
Our house is in the historic district of Chestertown, a 2 block walk from both Wash College and C’town waterfront. It has 2 primary bedroom suites. There are 3 more bedrooms, 1 is a loft which connected to the a 2nd story bedroom. There is a fenced yard. Out the garden gate is over an acre of garden.
We also host Carriage House Hideaway, a 2 person studio, behind Wren Retweet.
Over the years, we have stayed in a lot of Airbnbs, 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.
7. Fast internet that can accommodate many devices, streaming movies, and
and video conferencing.
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.
We live next door but will not bother you. We are always available by text.
Quiet dead end street in the heart of Chestertown’s historic district. In the middle of everything but totally private with beautiful gardens to wander in.
Park your car for your stay. You can walk to downtown Chestertown in 2 minutes!
No smoking on property.
No one under 25 can be primary renter.
No parties
Our prices include all fees. No hidden fees.
Add dates for prices
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Pets allowed: dogs and cats less than 218 lbs per pet (limit one pet total)
One time $20 pet fee
default
Smoking
Smoking is not permitted
No smoking on property.
Important information
You need to know
Property # 2003834
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
Note from host: No parties.
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, a first aid kit, and a deadbolt lock
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
About the neighborhood
Chestertown
Chestertown is home to this vacation home. Chesapeake Bay and Chestertown Historic District reflect the area's natural beauty and area attractions include Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Crumpton Auction and The Mainstay are also worth visiting.
Garfield Center for the Arts at the Prince Theater - 6 min walk - 0.6 km
Historical Society of Kent County Maryland - 8 min walk - 0.7 km
Washington College - 8 min walk - 0.7 km
Chestertown Historic District - 8 min walk - 0.7 km
Getting around
Baltimore, MD (MTN-Martin State) - 105 min drive
Restaurants
Milano's Pizzeria - 4 min drive
McDonald's - 3 min drive
Dunkin - 2 min drive
Procolino's - 3 min drive
Royal Farms - 4 min drive
Frequently asked questions
Is Wren Retweet- Country Estate in Center of C’Town pet-friendly?
Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 218 lbs per pet.
How much does it cost to stay at Wren Retweet- Country Estate in Center of C’Town?
As of Jun 18, 2026, prices found for a 1-night stay for 2 adults at Wren Retweet- Country Estate in Center of C’Town on Sep 21, 2026 start from $459, 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?
Onsite parking is available at the property.
What time is check-in at Wren Retweet- Country Estate in Center of C’Town?
Check-in begins at 4:00 PM.
What time is check-out at Wren Retweet- Country Estate in Center of C’Town?
Check-out is at 11:00 AM.
Where is Wren Retweet- Country Estate in Center of C’Town located?
Situated in Chestertown, this vacation home is within a 10-minute walk of Garfield Center for the Arts at the Prince Theater, River Arts Chestertown, and Chestertown Historic District. Historical Society of Kent County Maryland and Washington College are also within 10 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
This house is so lovely that it is a destination in itself. It has a happy vibe. Beautiful decor, tall ceilings, nice clean bathrooms with plenty of towels. The kitchen is very large & has everything! It is pet-friendly & also grandma friendly. We had a great time.
Beautiful kitchen so whole family could cook dinner together Friday night before soiree at Brittland Manor. Patio out back, perfect for sipping coffee and chatting. Close to town, lots of places to walk to - including farmer's market and the college.
We've stayed at a lot of places, but this was by far our favorite--a delightful historic and completely updated house, with a spectacular kitchen. All within walking distance of Chestertown's charming shopping district. Would definitely recommend!
Len L.
Stayed 4 nights in Nov 2023
Response from VrboOwner on Nov 28, 2023
You are the most wonderful guests! We so much appreciate you staying with us and hope you come back again!
Home is meticulously maintained, located on a quiet cut de sac. Walking distance to the restaurants and shops on Main St. Wonderful amenities -- coffee bar, bottled water, etc.
We felt at home, comfortable and welcomed. Great to be in walking distance to charming Chestertown, a safe and lovely town with a super Saturday market.
The property was perfect. Comfortable and spacious while retaining the historic elegance. Hosts were amazing. Answered questions/requests quickly. We had a fantastic stay and cant wait to return.
In the words of my wife: if we could give this house 10 stars, we would. Every detail is thought out, very well appointed property, great hosts. Highly recommended
We had a wonderful time. Our hosts were great and communication was timely and very accommodating. The home and grounds were a great setting for our vacation. We were most grateful for the special touches that made us feel quite welcome. Thank you!
Tom L.
Stayed 5 nights in Aug 2021
Response from VrboOwner on Aug 26, 2021
We really enjoyed meeting you and your lovely family! Hope you return.
This house was so beautifully restored with a beautiful family room, dining area for family dinners and comfortable beds. The gardens are spectacular!
It feels like a retreat but only a block from High and Cross Streets. We loved it.
Beautiful renovation of historic home with spacious kitchen and four lovely bedrooms. One block from restaurants/spas etc but on quiet side street with charming large garden. Gracious host; well stocked home. A great find!
We absolutely loved our stay here. The owners put a lot of effort and love into this property. Very beautiful and clean! They supply everything you need and more. Nice little town as well, right near the river and only a short trip to the beaches. We hope to return next summer and can’t wait to stay here again! Thank you!
Dominick B.
Stayed 1 night in Aug 2020
Response from VrboOwner on Aug 29, 2020
Thank you so much! We were so happy to host you and your adorable family! We really appreciate the great respect you showed for our house. Please come back anytime!!!