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Riverside at Pear Tree Point--Waterfront Escape

Photo gallery for Riverside at Pear Tree Point--Waterfront Escape

A spacious kitchen with a large island, a dining area with a view of the lake, and a blue sofa. - Riverside at Pear Tree Point--Waterfront Escape (Chestertown)
A spacious kitchen with white cabinetry, a large island with stools, a ceiling fan, and a view of greenery outside. - Riverside at Pear Tree Point--Waterfront Escape (Chestertown)
A covered outdoor area with a view of a lake, a wooden deck, and a wicker chair with cushions. - Riverside at Pear Tree Point--Waterfront Escape (Chestertown)
A modern two-story house with a large balcony, a covered porch, and a well-maintained lawn. - Riverside at Pear Tree Point--Waterfront Escape (Chestertown)
A spacious living room with a sectional sofa, a wooden coffee table, and a patterned rug. - Riverside at Pear Tree Point--Waterfront Escape (Chestertown)
Consider a stay at Riverside at Pear Tree Point--Waterfront Escape and take advantage of a firepit, a playground, and an arcade/game room. Stay connected with free in-room WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices), and guests can find other amenities such as laundry facilities.

Entire home

3 bedrooms2 bathrooms

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Parking available

Add dates for prices

About this property

Riverside at Pear Tree Point--Waterfront Escape

  • 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.

Property amenities

Beach

  • Beach loungers

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Wheelchair-accessible parking and van parking available

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Outdoor furniture
  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 2 accessible parking spaces
  • No elevator
  • Wheelchair accessibility
  • Wheelchair-accessible parking
  • Wheelchair-accessible van parking
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Things to do

  • Arcade/game room
  • Foosball table
  • Pickleball
  • Tennis
  • Basketball nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights
Failure to complete these may result in a negative review from the host.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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

We should mention

This property does not have elevators

About the area

Chestertown is home to this vacation home. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Visit our Chestertown travel guide
View more Vacation homes in Chestertown
Map
Chestertown, MD

What's nearby

  • A field of soybeans with a barn and silos in the background.
    Washington College
    11 min drive - 8.7 km
  • A building with a clock tower and cherry blossoms.
    Delaware State University
    56 min drive - 64.7 km
  • A stadium with spectators seated in rows.
    Dover International Speedway
    64 min drive - 66.1 km
  • Roundtop Park
    16 min walk - 1.4 km
  • Dover Downs Casino
    59 min drive - 66.1 km

Getting around

  • Baltimore, MD (MTN-Martin State)
    123 min drive

Restaurants

  • Milano's Pizzeria
    11 min drive
  • McDonald's
    14 min drive
  • Dunkin
    13 min drive
  • Procolino's
    13 min drive
  • Royal Farms
    10 min drive

Frequently asked questions

Is Riverside at Pear Tree Point--Waterfront Escape pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Riverside at Pear Tree Point--Waterfront Escape?

Check-in begins at 4:00 PM.

What time is check-out at Riverside at Pear Tree Point--Waterfront Escape?

Check-out is at 10:00 AM.

Where is Riverside at Pear Tree Point--Waterfront Escape located?

Located in Chestertown, this family-friendly vacation home is 0.7 mi (1.1 km) from Roundtop Park, and within 6 mi (10 km) of Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Kings Town Park and Chestertown Historic District are also within 6 mi (10 km).

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