See all properties
Entire home·Private host

Country Estate in Historic District

Choose dates to view prices

Photo gallery for Country Estate in Historic District

Fridge, microwave, oven, stovetop
Exterior detail
Terrace/patio
Property grounds
Interior

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Washer
  • Parking available
  • Barbecue grill
  • Air conditioning
  • Kitchen
  • Dryer

Explore the area

Map
Chestertown, MD
  • River Arts Chestertown
    ‪6 min walk‬
  • Historical Society of Kent County Maryland
    ‪7 min walk‬
  • Washington College
    ‪8 min walk‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪48 min drive‬

Room options

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.
This holiday home's walkable location gets good marks from our customers. During your stay, you're just a quick walk from Garfield Center for the Arts at the Prince Theater. The holiday home offers free WiFi and a kitchen.
  • Air-conditioned home with kitchen, washing machine and 3.5 bathrooms
  • Free WiFi
  • Within a 10-minute walk of Garfield Center for the Arts at the Prince Theater and River Arts Chestertown
Country Estate in Historic District offers its guests barbecue grills and a garden. The front desk is open around the clock.

Property manager

Robert Kestell

Languages

Portuguese, Spanish

Property amenities

Beach

  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

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

  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property
  • Note from host: No smoking on property.

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

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

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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 are welcome
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
    • Service animals are exempt from fees.
  • Note from host: One time $20 pet fee

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Property is also known as

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

Country Estate in Historic District Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 66 out of 66 reviews
Rating 8 - Good. 0 out of 66 reviews
Rating 6 - Okay. 0 out of 66 reviews
Rating 4 - Poor. 0 out of 66 reviews
Rating 2 - Terrible. 0 out of 66 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Diana M.

Liked: Cleanliness
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

Alisa R.

Liked: Cleanliness
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

ira d.

Liked: Cleanliness
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

Michael D.

Liked: Cleanliness
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
Best place ever
Wonderful place with great hosts
Stayed 2 nights in Dec 2023

10/10 Excellent

susan s.

Liked: Cleanliness
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., Columbia

Liked: Cleanliness
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

Stephen C.

Liked: Cleanliness
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

Sondra W.

Liked: Cleanliness
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
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
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

Chris W.

Liked: Cleanliness
Great stay!
Great stay!
Stayed 2 nights in Oct 2023

10/10 Excellent

Dmitry K.

Liked: Cleanliness
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
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
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
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
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
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

10/10 Excellent

Dawn M.

Liked: Cleanliness
Historic Charm with a Modern Flair
As others have stated, the pictures of this property do not do it justice. The owners have attended to every detail in this beautifully appointed home. The house was spotless, with quality linens and towels, and very comfortable beds. It is only a short walk to the cute downtown area. Beth and Robert live next store and are very friendly, while respectfully providing as much privacy as desired. We would definitely recommend!
Stayed 2 nights in Apr 2023

10/10 Excellent

sue B.

Liked: Cleanliness
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

10/10 Excellent

Mary S., Alexandria, Virginia

Liked: Cleanliness
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

Stacy S.

Liked: Cleanliness
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

Susan N.

Liked: Cleanliness
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

10/10 Excellent

Walter B.

Liked: Cleanliness
Excellent Stay
Stayed here for hunting trip. Hosts were extremely hospitable. Turned on football game in tv prior to our arrival so it was on when we got there. Very nice house with historic charm. Walking distance to downtown restaurants. Kitchen and family room were large and perfect for hanging out. Thank you. We’ll be back.
Stayed 2 nights in Jan 2023

10/10 Excellent

Kyle W.

Liked: Cleanliness
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