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Entire home

Country Estate in Historic District

Family-friendly vacation home in Chestertown

Photo gallery for Country Estate in Historic District

Fridge, microwave, oven, stovetop
Exterior detail
Interior
Exterior detail
Property grounds
Historic Chestertown charm meets modern comfort at this beautiful home. Step into a first-floor bedroom with private bath, explore the secluded yard, and enjoy gas grilling on the patio. With comfortable beds and quality linens, well-equipped kitchen amenities await in this peaceful retreat.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Barbecue grill

Add dates for prices

About this property

Entire place

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

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.

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
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

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

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

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

Outdoor areas

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

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

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

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center

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

  • Garden

Similar properties

Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
10.0 out of 10, Exceptional, 76 reviews
Circa 1900 Home in the Heart of Historic Downtown Chestertown

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

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Restrictions apply; for more information contact the property at the number on the booking confirmation
Note from host: One time $20 pet fee

Children and extra beds

Children are welcome

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 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

Property is also known as

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

About the neighborhood

Map
MD, Chestertown

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

  • Baltimore, MD (MTN-Martin State) - 105 min drive

Restaurants

  • ‪Royal Farms - ‬5 min walk
  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin - ‬2 min drive
  • ‪Procolino's - ‬3 min drive
  • ‪Subway - ‬18 min walk

Frequently asked questions

Is Country Estate in Historic District pet-friendly?

Yes, pets are allowed at this property. Some restrictions may apply, so please contact the property for more details.

What time is check-in at Country Estate in Historic District?

Check-in begins at 4:00 PM.

What time is check-out at Country Estate in Historic District?

Check-out is at 11:00 AM.

Where is Country Estate in Historic District located?

Located in the center of Chestertown, this family-friendly vacation home is within a 10-minute walk of Garfield Center for the Arts at the Prince Theater, Chestertown Historic District, and Wilmer Park. Historical Society of Kent County Maryland and Sumner Hall are also within 10 minutes.

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Reviews

Country Estate in Historic District Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 70 out of 70 reviews
Rating 8 - Good. 0 out of 70 reviews
Rating 6 - Okay. 0 out of 70 reviews
Rating 4 - Poor. 0 out of 70 reviews
Rating 2 - Terrible. 0 out of 70 reviews

Reviews

10/10 Excellent

Chris W.

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

Great stay!

Great stay!
Stayed 2 nights in Oct 2023

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

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

10/10 Excellent

Mary S., Alexandria, Virginia

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

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

10/10 Excellent

Diana M.

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

WHAT A JEWEL

Wow! This house is beautiful. A gem of old and new areas with lovely finishes and lots of space, each of us four guests had our own bedroom. The owners have supplied this domicile with every amenity one could imagine. It was well stocked with towels, paper products, kitchen tools and wonderful appliances. On the island stood a welcoming bottle of wine. Having enjoyed our stay so much, We may be returning next year!
Stayed 3 nights in Oct 2024

10/10 Excellent

Stacy S.

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

Charming home in a charming town!

This house is fantastic! From the tasteful decor to the radiant heated floors, it was a pleasure staying here. Wonderful fully appointed kitchen we actually could cook in, and very comfy beds and pillows! Hosts responded quickly to get a little wi-if issue resolved within 10 minutes! Can’t say enough good things about how great it is. We are returning and even extended our stay to enjoy the house again and the beautiful outside spaces!
Stayed 2 nights in Mar 2023

10/10 Excellent

Alisa R.

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

Owner wonderful to work with; walk to downtown Chestertown.

VRBO screwed up our booking and the owner took great pains to help us rebook a different property that they own in the neighborhood. She went above and beyond to make sure that our vacation went smoothly and communicated well with us every step of the way. What could have been an awful experience turned out to be a wonderful one. We had a great vacation. Head's up to other customers out there: VRBO has messed up 3 of our bookings this past 12 months. Make sure you DM the owner to ensure that everything is done correctly.
Stayed 6 nights in Jul 2024

10/10 Excellent

Kyle W.

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

Exemplary!

Everything about this property is perfection. It’s like walking into a brand new 1920s house. The charm is all there in spades, but the woodwork and hardware are in mint condition throughout. It’s the most perfectly kept old house I’ve ever stayed in. All that, but there are modern touches, too. The kitchen is huge and well stocked, and the main bath has a huge jacuzzi tub. Our dog had a blast running around the large park-like yard. The house is close to everything in town. The hosts were quick to respond. It was just a fantastic visit in every way. We hope to come back with friends soon!
Stayed 2 nights in Jan 2023

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

10/10 Excellent

Gwen R.

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

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

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

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

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

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

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

10/10 Excellent

Ann S.

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

Utterly GORGEOUS home and FANTASTIC hosts

I cannot say enough good things about our stay at Robert & Beth's home. The listing photos truly don't do justice to this home. It has beautiful historic details (warm, rich woodwork; built in shelving; a doorbell that you turn like a bike bell...) but doesn't feel stuffy or fragile. There is SO much living space to spread out in that our group of six never felt at all cramped. You can easily accommodate four couples or three couples and a family in this home. (The converted attic has two day beds and is accessed THROUGH one of the bedrooms, so not ideal for a 4th couple.) The outdoor space is also lovely. The house has a small, enclosed backyard with a patio table. A great place for happy hour or a sunny breakfast. You can go through the gate to Robert & Beth's adjoining huge garden. The home is as well appointed as the listing describes. And every night stand has a charging station with 3 plugs & 2 USB-As. Not sure if the listing mentioned that. Beth is about the most responsive host we've ever stayed with. I sent several questions before and during our stay and always had a response in under an hour - usually, within minuts. She also sent several suggestions for restaurants in town. No one was staying before or after us, so Robert & Beth graciously allowed us to arrive early and stay for a few extra hours. I would one MILLION PERCENT recommend staying here if you are going to Chestertown.
Stayed 2 nights in Oct 2023

10/10 Excellent

Cookie S.

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

Fabulous house

We absolutely loved this house. It was beautiful and immaculate and had everything you would need for your stay. Beth and Bob, the hosts were wonderful to deal with and we really enjoyed chatting with them. We were there for a wedding and wished we had more time to spend in the house since it was so fabulous. It was a quick walk to town and the perfect location. We would highly recommend this house!! Thank you again to Beth and Bob!!
Stayed 2 nights in Oct 2023

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

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

10/10 Excellent

Amy D., Collegeville, PA, USA

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

Chestertown Fun

We were a group of family and friends in Chestertown for a week. Bob and Beth have a beautiful, comfortable house, and there was plenty of room for the seven of us. The house was very clean. The kitchen is equipped with everything you need to have a nice dinner at home. We liked the wine refrigerator, too. We will definitely stay at this property again.
Stayed 8 nights in Jul 2023

10/10 Excellent

Donna L.

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

Great property

This home was perfect for our family visit. The gardens were so beautiful. The town was just up the block and friendly with shops and restaurants and a Saturday farmers market. The beds were comfortable. The space was homie and convenient. The 6 year old looks up at me on our last night and says. Grandma can’t we just stay here longer. I think we found a winner.
Stayed 6 nights in Jun 2023

10/10 Excellent

Peter T.

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

A beautiful home. Enjoyed it very much.

Trouble with air conditioning first day. After that everything was great. Very beautiful home,
Stayed 4 nights in Jun 2023

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