Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit | House in Chestertown
3 Bedroom House in Chestertown
NEW: Private hot tub available for stays beginning October 5, 2026!
Welcome to Pear Tree Point, a private waterfront retreat on the Chester River near historic Chestertown, Maryland. Relax in the 6-person hot tub on the covered deck, gather around the waterfront fire pit, or simply settle in and enjoy peaceful river views.
Perfect for families, couples, and small groups, the home offers plenty of space to be together while still giving everyone room to spread out.
Inside, the main level features a comfortable living area, fully equipped kitchen, and beautiful water views. Step outside onto the covered deck for morning coffee overlooking the river or an evening soak in the hot tub.
The walkout lower level provides a second family room with built-in bunk beds and a full bathroom, making it a great space for kids or additional guests. With two separate living areas, the home works especially well for families and groups traveling together.
Outside, enjoy the spacious waterfront property, fire pit, covered deck, and hot tub. Take in views of the Chester River on one side and horses grazing in the neighboring pasture on the other. Whether you're starting the morning by the water or winding down under the stars, it's a peaceful setting that feels removed from it all.
When you're ready to explore, pickleball, basketball, and tennis courts are less than half a mile away. Downtown Chestertown is just a short drive away, with local restaurants, shops, waterfront areas, and historic Eastern Shore charm.
Whether you're planning a family getaway, couples' weekend, or simply looking for a quiet waterfront escape, Pear Tree Point offers a comfortable home base for enjoying Maryland's Eastern Shore.
PROPERTY HIGHLIGHTS
• Private 6-person hot tub on the covered deck
• Waterfront setting with beautiful Chester River views
• Waterfront fire pit
• Covered deck and outdoor gathering spaces
• Two separate indoor living areas
• Walkout lower-level family room with built-in bunk beds
• Fully equipped kitchen
• Multiple bathrooms
• Less than 1/2 mile to pickleball, basketball, and tennis courts
• Short drive to historic downtown Chestertown
• Quiet, private setting
SLEEPING ARRANGEMENTS
• Primary bedroom – Queen Bed
• Bedroom 2 –Queen Bed
• Lower-level bunk area – Built-in bunk beds in the family room with Double Beds on the bottom level and single bunks above.
Guests have private access to the home and waterfront property during their stay. We're also happy to provide local recommendations for exploring Chestertown and Maryland's Eastern Shore.
Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit is located in Chestertown. Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit provides accommodation, featuring Balcony/Terrace, Barbecue/Outdoor Cooking, Heating, among other amenities. This House features Air Conditioner, Parking and TV to make your stay a comfortable one.
Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit 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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Bathtub or shower
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2 bathrooms
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Soap
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Shampoo
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Jetted bathtub
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Towels provided
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Toilet paper
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Hair dryer
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Bed sheets provided
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3 bedrooms
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Dining room
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Dining table
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Oven
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Stovetop
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Lobster/crab pot
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Paper towels
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Refrigerator
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Dishwasher
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Kitchen island
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Toaster
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Microwave
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Washing machine and dryer
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Laundry facilities
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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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Wheelchair-accessible van parking
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Wheelchair-accessible parking
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Wheelchair accessible
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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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2 on-site accessible parking spaces
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No elevators
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Marina nearby
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Basketball nearby
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Pickleball court
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Tennis on site
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Birdwatching nearby
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Arcade/game room
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Smart TV
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Foosball table
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On the waterfront
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Near a river
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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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Firepit
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Patio
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Barbecue grill
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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
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Hot tub
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 special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed onsite parties or group events are strictly prohibited host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property safety features at this property include a fire extinguisher 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 property 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 property 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 property?
Best-rates for the Chestertown house starts from $527 per night with includes Entertainment, Parking, TV, Accessibility, Wellness Facilities, Guest Services, Air Conditioner, Security/Safety, Child Friendly, Kitchen, View, Sports/Activities, Bedding/Linens, Hot Tub, Balcony/Terrace, Barbecue/Outdoor Cooking, Heating, Internet, Laundry with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is property 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 property 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 property?
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 property?
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.
