Country Estate in Historic District

5.0

Outstanding(65 Reviews)

House in Chestertown, MD

10 guests · 5 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Free cancellationFull refund if you change your mind

Great for petsBring all your friends and family, even the furry ones

About this house rental

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.

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Laundry

Balcony or Patio

Dishwasher

Garden

Family friendly

Map of Chestertown, MD

Nearby attractions

The Walters Art Museum

48.2 mi

Fort McHenry National Monument and Historic Shrine

44.6 mi

$$$$

Country Estate in Historic District

$$$$

5.0

Outstanding(65 Reviews)

House in Chestertown, MD

10 guests · 5 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Free cancellationFull refund if you change your mind

Great for petsBring all your friends and family, even the furry ones

About this house rental

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Laundry

Balcony or Patio

Dishwasher

Garden

Family friendly

Map of Chestertown, MD

Nearby attractions

The Walters Art Museum

48.2 mi

Fort McHenry National Monument and Historic Shrine

44.6 mi

Reviews

5.0

Outstanding(65 Reviews)

5.0

Jul 2024

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.

5.0

Jul 2024

Lovely property, a nice anniversary get away for us. Thank you for the generosity and kindness to our hosts Beth and Bob.

5.0

Mar 2024

Place is FABULOUS!!! Fantastic location easy to walk around town. THANKS FOR EVERYTHING

5.0

Dec 2023

Wonderful place with great hosts

5.0

Dec 2023

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.

5.0

Nov 2023

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!

5.0

Nov 2023

The home is beautiful! Beth and Bob took great care of us. I look forward to staying there again!

5.0

Nov 2023

Thank you! The family enjoyed their stay and loved the ambiance of your B&B and of Chestertown. 🙏❣️👏

5.0

Oct 2023

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.

5.0

Oct 2023

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!!

5.0

Oct 2023

Great stay!

5.0

Oct 2023

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

5.0

Aug 2023

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.

5.0

Jul 2023

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.

5.0

Jul 2023

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.

5.0

Jun 2023

Trouble with air conditioning first day. After that everything was great. Very beautiful home,

5.0

Apr 2023

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.

5.0

Apr 2023

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!

5.0

Apr 2023

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.

5.0

Apr 2023

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!

5.0

Mar 2023

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!

5.0

Jan 2023

A lovely home and amenities. We had a winderful stay.

5.0

Jan 2023

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.

5.0

Jan 2023

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!

5.0

Jan 2023

The house felt larger than expected based on the photos. It was very beautifully decorated and also comfortable. There was a lot of old house detail and charm but also had updated baths and kitchen. Our stay was very short and the weather was cold so we didn’t get to fully take advantage of the lovely garden or well equipped kitchen but we can see ourselves back here again to visit our family. Great communication with owners as well!

5.0

Dec 2022

We thoroughly enjoyed our stay in Chestertown. The house is beautiful with comfortable bedrooms rooms, delightful sitting areas, super well equipped kitchen, and luxury bathrooms. Hosts were delightful. We highly recommend it.

5.0

Nov 2022

Perfect location. Very comfortable.

5.0

Oct 2022

Loved this property. So beautiful and well equipped. Beds were very comfy. Walking distance to everything in town.

5.0

Oct 2022

A beautiful home. Spotless. Absolutely perfect!!

5.0

Sep 2022

The host were friendly and the check in and out went flawlessly. The house was stunning.

5.0

Sep 2022

Great house, lovely owners. No complaints at all!!

5.0

Sep 2022

This was the second time we stayed at this property. The house is lovely, contains everything we needed for a comfortable and relaxing vacation and is situated within easy walking distance of the town center and waterfront. Thank you again!

5.0

Sep 2022

Beautiful and well appointed home. We enjoyed updated kitchen and bathrooms, beautiful backyard, easy parking.

5.0

Aug 2022

My family and friends really liked our stay here. Great kitchen, comfy beds, and close to town. Would definitely stay here again.

5.0

Jul 2022

Immaculate!

Immaculate!

We were so delighted to stay at this beautiful home in downtown Chestertown. The property was immaculate and a rare find. This was the antithesis of a typical historic home; the renovations combining new and old were seamless, the home was very clean and critter free and the love and attention our hosts have showered on the property is evident inside and out. The house is perfectly situated on a street where people spend time to garden and perfect their homefronts, and within walking distance of the Saturday street market. Robert and Beth were fabulous hosts, and although we didn't spend much time at the property (we were attending a family reunion), we felt very assured they were there for anything we might need.

5.0

Jul 2022

Luxurious Tranquility

Luxurious Tranquility

Excellent property conveniently located in historic Chestertown. Easy to walk to the river, downtown and the college. The property is tastefully appointed with all the amenities needed. It is only exceeded by the wonderous landscaping and secret garden-like backyard. Truly a jewel of a place.

5.0

May 2022

Perfect spot for our sisters reunion!

Perfect spot for our sisters reunion!

This is an absolutely beautiful property, just exactly as pictured. Beth and Robert were extremely accessible and responsive. We are already planning next year's meeting!

5.0

Apr 2022

Fantastic!

Fantastic!

Bob and Beth’s place is beautiful, clean, and comfortable. We enjoyed cooking in the spacious kitchen and walking through the beautiful gardens. We loved our stay and will definitely be back!

5.0

Mar 2022

Chestertown Stay

Chestertown Stay

Great house. Very clean and great location

5.0

Mar 2022

Beautiful house in downtown Chester town

Beautiful house in downtown Chester town

Beautiful house with all the amenities you could need large rooms great kitchen with everything needed very spacious house enjoyed our stay was 8 adults and had plenty of room

FAQs

How much does this house cost compared to others in Chestertown?

The average price for a rental in Chestertown is $292 per night. This rental is $596 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Country Estate in Historic District. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Country Estate in Historic District pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Country Estate in Historic District?

We found 12 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.

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3.8

Good(231 Reviews)

Comfort Inn & Suites Chestertown

Hotel

in Chestertown

2-star

2 queen beds

Pets allowed · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Chestertown? Our Hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.

$$$$

Country Estate in Historic District

House in Chestertown, MD

Reasons to book

About this house rental

Amenities

Map of Chestertown, MD

Nearby attractions

Country Estate in Historic District

House in Chestertown, MD

Reasons to book

About this house rental

Amenities

Map of Chestertown, MD

Nearby attractions

Reviews

FAQs

How much does this house cost compared to others in Chestertown?

Is parking included with this house?

Is there a pool at this house?

Is Country Estate in Historic District pet friendly?

What amenities are available at Country Estate in Historic District?

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