Country Estate in Historic District | House in Chestertown

10.0 (74 Reviews) |   Pet Friendly   5 Bedrooms  3 Bathrooms  10 Guests
Chestertown House | Country Estate in Historic District

5 Bedroom House in Chestertown

History with modern convenience, including first floor bedroom with private bath and super fast internet.
Our house is in the historic district of Chestertown, a 2 block walk from both Wash College and C’town waterfront. It has 2 primary bedroom suites. There are 3 more bedrooms, 1 is a loft which connected to the a 2nd story bedroom. There is a fenced yard. Out the garden gate is over an acre of garden.
We also host Carriage House Hideaway, a 2 person studio, behind Wren Retweet.
Over the years, we have stayed in a lot of Airbnbs, 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.
7. Fast internet that can accommodate many devices, streaming movies, and
and video conferencing.
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.
We live next door but will not bother you. We are always available by text.
Quiet dead end street in the heart of Chestertown’s historic district. In the middle of everything but totally private with beautiful gardens to wander in.
Park your car for your stay. You can walk to downtown Chestertown in 2 minutes!
No smoking on property.
No one under 25 can be primary renter.
No parties

Country Estate in Historic District is located in Chestertown. Country Estate in Historic District provides accommodation, featuring Air Conditioner, Parking, Pet Friendly, among other amenities. This House features Air Conditioner, Parking, Pet Friendly, to make your stay a comfortable one.

Country Estate in Historic District has 5 Bedrooms , 3 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chestertown has interesting places to visit. If you want to learn more about the House in Chestertown, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Heating
  • Air conditioning
Bathrooms
  • Hair dryer
  • Towels provided
  • Shower
  • Shampoo
  • 4 bathrooms
  • Soap
  • Toilet paper
Bedroom
  • 5 bedrooms
  • Bed sheets provided
  • Dining table
  • Fireplace
  • Dining room
  • Living room
Kitchen
  • Coffee/tea maker
  • Oven
  • Coffee grinder
  • Ice maker
  • Microwave
  • Stovetop
  • Dishwasher
  • Refrigerator
  • Paper towels
Laundry
  • Washing machine and dryer
  • Laundry facilities
Ocean view
  • Beach sun loungers
  • Beach towels
Parking
  • Onsite parking
Pet Friendly
  • Welcoming cats and dogs only
  • Pet friendly
  • 1 total (up to 218 lbs per pet)
Accessibility
  • Note from host: No smoking on property.
  • Smoke-free property
Entertainment
  • Games
  • Smart TV with cable/satellite service
  • Stereo
  • Books
General
  • Property does not allow children
  • Spanish
  • Portuguese
  • Desk
  • Desk chair
Guest Services
  • Travel crib
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Balcony
  • Fenced yard
  • Gas grill
  • Garden
  • Outdoor furniture
  • Firepit
Security/Safety
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Fire extinguisher
  • First aid kit
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Deadbolt lock

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
Child Policy
This property does not allow children.
Event Policy
No events allowed;no parties.
Pet Policy
1 total (up to 218 lbs per pet) note from host: one time $20 pet fee pets allowed service animals are welcome, and are exempt from fees welcoming dogs and cats only
Smoking Policy
Smoking is not permitted;no smoking on property.

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property note from host: no parties. onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room 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

Reviews

Joyce D.
Jan 22, 2026 12:21:10 AM
Review Score:   10
Summary: 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.
See All Reviews

FAQ's

Is this Chestertown house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chestertown house have a swimming pool?

No, this Chestertown house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chestertown house?

Best-rates for the Chestertown house starts from $440 per night with includes Ocean View, Balcony/Terrace, Security/Safety, Sports/Activities, Bedding/Linens, Wellness Facilities, Internet, Laundry, View, Entertainment, Air Conditioner, Parking, Pet Friendly, Fireplace/Heating, Guest Services, Barbecue/Outdoor Cooking, Child Friendly, Kitchen, TV with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Chestertown house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chestertown house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chestertown house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chestertown house?

Based on the information reported by the owner or manager, the Chestertown house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chestertown house?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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