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Wren Retweet- Country Estate in Center of C’Town

Chestertown vacation home with kitchen

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Photo gallery for Wren Retweet- Country Estate in Center of C’Town

A park with a curved wooden bridge, a tree with purple blossoms, and a grassy area.
A porch with a red door, a bench, and potted plants.
A bedroom with a large bed, wooden bookshelves, a tall black column, and large windows.
A kitchen with a central island, wooden cabinets, a ceiling fan, and a dining area with a chair and rug.
A wooden cabinet with glass doors, a red carpet, and a patterned rug in a hallway.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Chestertown, MD
  • Place, Garfield Center for the Arts at the Prince Theater
    ‪6 min walk‬
  • Place, Washington College
    ‪8 min walk‬
  • Place, Chestertown Historic District
    ‪8 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 min drive‬

Room options

About the neighborhood

Chestertown

In Chestertown .Within a 10-minute walk of the vacation home, you'll find Garfield Center for the Arts at the Prince Theater and River Arts Chestertown. Chestertown Historic District and Historical Society of Kent County Maryland are also within half a mile (1 km).
View more Vacation Homes in ChestertownOpens in a new window

What's nearby

  • River Arts Chestertown - 5 min walk - 0.3 miles
  • Garfield Center for the Arts at the Prince Theater - 6 min walk - 0.4 miles
  • Historical Society of Kent County Maryland - 8 min walk - 0.5 miles
  • Washington College - 8 min walk - 0.5 miles
  • Chestertown Historic District - 8 min walk - 0.5 miles

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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  • Kitchen
  • Dryer
  • Parking included
  • Air conditioning
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Property amenities

Beach

  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Fenced yard
  • Firepit
  • Gas grill
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming cats and dogs only
  • One pet total (up to 218 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed
  • Note from host: No smoking on property.

Services and conveniences

  • Iron/ironing board

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
  • Deadbolt lock

General

  • Property does not allow children

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

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
  • Only dogs and cats are allowed
  • Maximum 1 (weight limit: 218 lbs per pet)
  • Service animals are exempt from fees
  • Note from host: One time $20 pet fee

Children and extra beds

  • This property does not allow children.

Events

No events allowed
No parties.

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
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
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 private host, not a professional engaged in trade or business. 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. Note from host: No parties. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

Estate In Historic District
564820
Country Estate in Historic District Chestertown
Country Estate in Historic District Private vacation home

Frequently asked questions

How close is Wren Retweet- Country Estate in Center of C’Town to the airport?

This vacation home is 73.2 mi (105-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

How much does it cost to stay at Wren Retweet- Country Estate in Center of C’Town?

As of Jul 25, 2026, prices found for a 1-night stay for 2 adults at Wren Retweet- Country Estate in Center of C’Town on Aug 25, 2026 start from $558, 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.

Does Wren Retweet- Country Estate in Center of C’Town have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Wren Retweet- Country Estate in Center of C’Town to the beach?

This vacation home is 13 mi (26-min drive) from Betterton Beach and 13.6 mi (26-min drive) from Main Beach. Don't forget your sunscreen!

Does Wren Retweet- Country Estate in Center of C’Town offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Wren Retweet- Country Estate in Center of C’Town?

No, there is no casino at this vacation home.

What time is check-in at Wren Retweet- Country Estate in Center of C’Town?

Check-in begins at 4:00 PM.

Is there free parking at Wren Retweet- Country Estate in Center of C’Town?

Free parking is not available at this vacation home.

Does Wren Retweet- Country Estate in Center of C’Town have a pool?

This vacation home does not have a pool.

Does Wren Retweet- Country Estate in Center of C’Town have a spa?

There are no spa services available at this vacation home.

How close is Wren Retweet- Country Estate in Center of C’Town to downtown Chestertown?

This vacation home is 0.5 mi away from Chestertown.

Wren Retweet- Country Estate in Center of C’Town Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 75 out of 75 reviews
Rating 8 - Good. 0 out of 75 reviews
Rating 6 - Okay. 0 out of 75 reviews
Rating 4 - Poor. 0 out of 75 reviews
Rating 2 - Terrible. 0 out of 75 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Diana S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay.
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Connor J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is comfortable and roomy. The hosts are great. I’ll stay here every time I am in Chestertown!
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Robin G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great hosts, location, gardens, and overallstay!
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Joyce D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Chris W.

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

Great stay!

Great stay!
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Judie G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a lovely restored spacious comfortable home. We keep coming back! Friendly gracious hosts. Highly recommended’
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

David K.

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

Best place ever

Wonderful place with great hosts
Stayed 2 nights in Dec 2023
Verified

10/10 Excellent

Gwen R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was wonderful! Thank you!
Stayed 2 nights in May 2025
Verified

10/10 Excellent

ira d.

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

anniversary get away

Lovely property, a nice anniversary get away for us. Thank you for the generosity and kindness to our hosts Beth and Bob.
Stayed 2 nights in Jul 2024
Verified

10/10 Excellent

Susan N.

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

walking distance to downtown and historic Chestertown and campus. well located.

A lovely home and amenities. We had a winderful stay.
Stayed 2 nights in Jan 2023
Verified

10/10 Excellent

Margaret H.

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

Great stay in Chestertown

Loved this property. So beautiful and well equipped. Beds were very comfy. Walking distance to everything in town.
Stayed 3 nights in Oct 2022
Verified

10/10 Excellent

Stephen C.

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

Excellent

The home is beautiful! Beth and Bob took great care of us. I look forward to staying there again!
Stayed 2 nights in Nov 2023
Verified

10/10 Excellent

Elder p.

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

Wedding Weekend

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.
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Len L.

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

The best place!

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!
Stayed 4 nights in Nov 2023
Verified

10/10 Excellent

Deborah K.

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

Beautiful property in middle of Chestertown

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.
Stayed 2 nights in Aug 2023
Verified

10/10 Excellent

Michael D.

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

Chestertown wedding

Place is FABULOUS!!! Fantastic location easy to walk around town. THANKS FOR EVERYTHING
Stayed 3 nights in Feb 2024
Verified

10/10 Excellent

sue B.

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

Welcome

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.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

susan s.

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

Great location and amazing house

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.
Stayed 2 nights in Dec 2023
Verified

10/10 Excellent

Dmitry K.

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

Amazing Property

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
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Tom L.

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

Great family vacation in Chestertown!

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!
Stayed 5 nights in Aug 2021
Verified

10/10 Excellent

Karen J.

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

perfect wedding weekend!

Wonderfully renovated historic property in the middle of town. Lots of room and super clean...Fresh flowers greeted us upon arrival. Just wonderful.
Stayed 4 nights in Aug 2021
Verified

10/10 Excellent

Mary Beth K.

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

Spectacular property

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.
Stayed 5 nights in Apr 2023
Verified

10/10 Excellent

Mary S.

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

Gorgeous historic home; perfect location

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!
Stayed 3 nights in Mar 2023
Verified

10/10 Excellent

Dominick B.

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

Beautiful house and property!

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!
Stayed 1 night in Aug 2020
Verified

10/10 Excellent

Sondra W.

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

November 2023

Thank you! The family enjoyed their stay and loved the ambiance of your B&B and of Chestertown. 🙏❣️👏
Stayed 2 nights in Nov 2023