House in Chestertown, MD
10 guests · 5 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this house rental
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 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
Amenities at Wren Retweet- Country Estate in Center of C’Town
Non-smoking
Pets allowed
Map of Chestertown, MD
Ratings and reviews
10 / 10Outstanding·Jan 2026
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.
10 / 10Outstanding·Jan 2026
The house is comfortable and roomy. The hosts are great. I’ll stay here every time I am in Chestertown!
10 / 10Outstanding·Jan 2026
The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay.
10 / 10Outstanding·Sep 2025
Such a lovely restored spacious comfortable home. We keep coming back! Friendly gracious hosts. Highly recommended’
$$$$
Top rated by guests
10Outstanding
(73 Ratings)
"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!..."
Joyce D.Don't miss out! Price and availability may change
