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Country Estate in Historic District

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Property grounds - Country Estate in Historic District (Chestertown)
Interior - Country Estate in Historic District (Chestertown)
Interior - Country Estate in Historic District (Chestertown)
Terrace/patio - Country Estate in Historic District (Chestertown)
Interior - Country Estate in Historic District (Chestertown)
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 102600 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning

Add dates for prices

About this property

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 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

  • Laundry facilities
  • 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
  • Unit size: 2,600 square feet

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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

Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed

Service animals are welcome, and are exempt from fees

Restrictions apply; for more information contact the property on 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

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

About the area

Located in Chestertown, this holiday home is in the city centre. Chesapeake Bay and Chestertown Historic District reflect the area's natural beauty and area attractions include Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Travelling with kids? Consider Crumpton Auction and The Mainstay. Visit our Chestertown travel guide
View more Holiday homes in Chestertown
Map
Chestertown, MD

What's nearby

  • Washington College
    Washington College
    8 min walk - 0.5 miles
  • 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
  • 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
  • Royal Farms
    4 min drive
  • Procolino's
    3 min drive

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.

How much is parking at Country Estate in Historic District?

On-site parking is available at the property.

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?

Checkout is at 11:00 AM.

Where is Country Estate in Historic District located?

Located in the centre of Chestertown, this family-friendly holiday 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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Country Estate in Historic District Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 74 out of 74 reviews
Rating 8 - Good. 0 out of 74 reviews
Rating 6 - Okay. 0 out of 74 reviews
Rating 4 - Poor. 0 out of 74 reviews
Rating 2 - Terrible. 0 out of 74 reviews

10

Cleanliness

10

Location

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

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

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

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

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

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

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
Verified

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
Verified

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
Verified

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
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

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

Robin G.

Liked: Check-in, communication, location
Nice property. Wish we had known there was no air conditioning. Lind of hot at night
Stayed 2 nights in Jun 2025
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

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