Riverside at Pear Tree Point-Waterfront Escape | House in Chestertown
3 Bedroom House in Chestertown
Welcome to Pear Tree Point, a peaceful waterfront retreat near historic Chestertown, Maryland. Perfect for families, couples, and small groups, this relaxing getaway offers beautiful river views, spacious gathering areas, and the perfect setting to unwind, reconnect, and enjoy the Eastern Shore.
The home features comfortable living spaces, modern amenities, and plenty of room for everyone to spread out and relax. The main level includes an open living area, fully equipped kitchen, and water views throughout the home. Step outside to enjoy the peaceful outdoor spaces, morning coffee by the river, or evenings spent relaxing with family and friends.
The walkout lower level offers a second family room with built-in bunk beds and a full bathroom, creating a fun and flexible sleeping and hangout area that’s perfect for kids or additional guests. Two separate living areas make the home especially comfortable for families and groups traveling together.
Guests can enjoy nearby pickleball, basketball, and tennis courts located less than a half-mile away, or explore the shops, restaurants, waterfront, and small-town charm of nearby Chestertown just a short drive away.
Whether you're visiting for a relaxing waterfront escape, a family getaway, boating and outdoor activities, or a peaceful weekend on Maryland’s Eastern Shore, Pear Tree Point provides the perfect place to slow down and make lasting memories.
PROPERTY HIGHLIGHTS
• Waterfront setting with river views
• Spacious indoor and outdoor gathering spaces
• Walkout lower level with bunk bed area and second family room
• Fully equipped kitchen
• Multiple living areas perfect for families and groups
• Less than 1/2 mile to pickleball, basketball, and tennis courts
• Short drive to downtown Chestertown
• Quiet and private setting ideal for relaxing getaways
SLEEPING ARRANGEMENTS
• Bedroom 1 – [King/Queen bed]
• Bedroom 2 – [King/Queen bed]
• Lower level bunk area – Built-in bunk beds located in the lower-level family room
You’ll have full private access to the home during your stay. We’re happy to provide local recommendations to help you enjoy everything Chestertown and Maryland’s Eastern Shore have to offer.
Riverside at Pear Tree Point-Waterfront Escape is located in Chestertown. Riverside at Pear Tree Point-Waterfront Escape provides accommodation, featuring Hot Tub, Internet, Laundry, among other amenities. This House features Hot Tub, Internet, Laundry, to make your stay a comfortable one.
Riverside at Pear Tree Point-Waterfront Escape has 3 Bedrooms , 2 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.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Facility Overview
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Heating
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Air conditioning
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Soap
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Bathtub or shower
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Towels provided
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Jetted bathtub
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2 bathrooms
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Toilet paper
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Hair dryer
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3 bedrooms
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Bed sheets provided
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Dining table
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Dining room
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Ice maker
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Oven
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Kitchen island
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Dishwasher
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Stovetop
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Microwave
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Coffee/tea maker
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Cookware/dishes/utensils
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Refrigerator
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Laundry facilities
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Washing machine and dryer
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Beach sun loungers
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Wheelchair-accessible parking and van parking available
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Onsite parking
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No pets allowed
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No elevators
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Smoke-free property
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If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
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Wheelchair-accessible van parking
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2 on-site accessible parking spaces
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Wheelchair-accessible parking
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Wheelchair accessible
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Basketball nearby
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Pickleball court
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Tennis on site
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Arcade/game room
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Smart TV
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Foosball table
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English
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Playground
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Iron/ironing board
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Free WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices)
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Outdoor furniture
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Barbecue grill
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Firepit
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Deck or patio
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Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
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Smoke detector installed (host has indicated there is a smoke detector on the property)
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Fire extinguisher
Policies
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 onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher 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
FAQ's
Is this Chestertown house pet-friendly for guests?
No, pets are not 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 $412 per night with includes Child Friendly, Air Conditioner, Parking, Accessibility, Barbecue/Outdoor Cooking, TV, Ocean View, Security/Safety, Hot Tub, Internet, Laundry, Sports/Activities, Bedding/Linens, Wellness Facilities, Fireplace/Heating, View, Balcony/Terrace, Kitchen 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.
