Country Estate in Historic District | House in Chestertown

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

Best-rates for the Chestertown house starts from $356 per night with includes Air Conditioner, Pet Friendly, Balcony/Terrace, Security/Safety, Child Friendly, Wellness Facilities, Fireplace/Heating, Entertainment, Barbecue/Outdoor Cooking, Kitchen, Bedding/Linens, Guest Services, Parking, TV, View, Ocean View, Sports/Activities, Internet, Laundry with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

10.0 (70 Reviews) | Pet Friendly 5 Bedrooms 3 Bathrooms 10 Guests

Chestertown House | Country Estate in Historic District

5 Bedroom House in Chestertown

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.

Country Estate in Historic District is located in Chestertown. Country Estate in Historic District provides accommodation, featuring Wellness Facilities, Fireplace/Heating, Entertainment, among other amenities. This House features Wellness Facilities, Fireplace/Heating, Entertainment, 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.

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

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 Children are welcome.

Pet Policy Note from host: one time $20 pet fee pets allowed restrictions apply; for more information contact the property at the number on the booking confirmation service animals are welcome, and are exempt from fees

Other Policy 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 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

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Reviews

Robin G. Jun 16, 2025 01:19:49 AM

Summary: Great hosts, location, gardens, and overallstay!

Gwen R. Jun 11, 2025 08:25:20 PM

Summary: Everything was wonderful! Thank you!

Elder p. May 5, 2025 02:08:59 AM

Summary: 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.

Diana M. Oct 20, 2024 11:25:43 AM

Summary: 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!

Alisa R. Jul 31, 2024 08:14:34 PM

Summary: 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.

ira d. Jul 6, 2024 10:58:45 PM

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

Michael D. Mar 3, 2024 06:22:35 AM

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

David K. Dec 17, 2023 04:47:57 AM

Summary: Wonderful place with great hosts

susan s. Dec 11, 2023 05:53:52 AM

Summary: 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.

Len L. Nov 28, 2023 11:40:43 AM

Summary: 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!

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 $356 per night with includes Air Conditioner, Pet Friendly, Balcony/Terrace, Security/Safety, Child Friendly, Wellness Facilities, Fireplace/Heating, Entertainment, Barbecue/Outdoor Cooking, Kitchen, Bedding/Linens, Guest Services, Parking, TV, View, Ocean View, Sports/Activities, Internet, Laundry with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

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?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chestertown house are as follows: Cancellation policy 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.

Check House Availability

Nightly rates from:

US $356