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Country Estate in Historic District

Family-friendly stay with in-room kitchens in Chestertown

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Photo gallery for Country Estate in Historic District

Fridge, microwave, oven, stovetop
Exterior detail
Property grounds
Interior
Exterior detail

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Kitchen

Explore the area

View in a map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪5 min walk‬
  • Place, Historical Society of Kent County Maryland
    ‪8 min walk‬
  • Place, Washington College
    ‪8 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪106 min drive‬

Room options

About the neighborhood

Chestertown

City center stay.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
  • 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
  • Wilmer Park - 9 min walk - 0.5 miles

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

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.

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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
  • 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

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
  • 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.

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
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. 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.

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

Frequently asked questions

How close is Country Estate in Historic District 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.

Does Country Estate in Historic District have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Country Estate in Historic District 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 Country Estate in Historic District offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Country Estate in Historic District?

No, there is no casino at this vacation home.

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

Check-in begins at 4:00 PM.

Is there free parking at Country Estate in Historic District?

Free parking is not available at this vacation home.

Does Country Estate in Historic District have a pool?

This vacation home does not have a pool.

Does Country Estate in Historic District have a spa?

There are no spa services available at this vacation home.

How close is Country Estate in Historic District to downtown Chestertown?

This vacation home is 0.5 mi away from Chestertown.

Country Estate in Historic District Reviews

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

10/10 Excellent

Judie G., Washington, DC

Liked: Cleanliness
Such a lovely restored spacious comfortable home. We keep coming back! Friendly gracious hosts. Highly recommended’
Stayed 3 nights in Sep 2025

10/10 Excellent

Robin G.

Liked: Cleanliness
Great hosts, location, gardens, and overallstay!
Stayed 2 nights in Jun 2025

10/10 Excellent

Gwen R.

Liked: Cleanliness
Everything was wonderful! Thank you!
Stayed 2 nights in May 2025

10/10 Excellent

Elder p.

Liked: Cleanliness

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

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