Entire home

Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit

Photo gallery for Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit

A hot tub with a view of a lake and trees.
A spacious kitchen with a large island, a dining area with a view of the lake, and a blue sofa.
A spacious kitchen with white cabinetry, a large island with stools, a ceiling fan, and a view of greenery outside.
A spacious living room with a sectional sofa, a wooden coffee table, and a patterned rug.
A modern two-story house with a large balcony, a covered porch, and a well-maintained lawn.

Reviews

10 out of 10
Exceptional

Highlights

  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.

Popular amenities

  • Spa pool on site
  • Patio
  • Arcade/game room
  • Barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Chestertown, MD
  • Place, Roundtop Park
    ‪16 min walk‬
  • Place, Rock Hall Harbor
    ‪33 min drive‬
  • Place, Dover Downs Casino
    ‪59 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪134 min drive‬

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 2

1 Queen Bed

Ground Level Bunk Area

1 Single Bunk Bed and 2 Double Beds

Primary Floor Bedroom

1 Queen Bed

2 bathrooms

Ground floor bathroom

Towels provided · Bathtub or shower · Toilet · Hair dryer

Primary floor bathroom

Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Dining area

Add dates for prices

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  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
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About the area

Chestertown

Located in Chestertown, this holiday home is on the waterfront. 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 Schooner Sultana. Travelling with kids? Consider Larrabee Arts Center and Crumpton Auction. Spend some time exploring the area's activities, including birdwatching.
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Map
Chestertown, MD

What's nearby

  • Roundtop Park - 16 min walk - 1.4 km
  • Rock Hall Harbor - 33 min drive - 35.6 km
  • Queenstown Harbor Golf - 44 min drive - 49.3 km
  • Delaware State University - 56 min drive - 64.7 km
  • Dover Downs Casino - 59 min drive - 66.1 km

Getting around

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

Restaurants

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

Frequently asked questions

Is Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit?

As of 7 November 2026, prices found for a 1-night stay for 2 adults at Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit on 16 November 2026 start from NZ$1,556, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit?

On-site parking is available at the property.

What time is check-in at Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit?

Check-in begins at 4:00 PM.

What time is check-out at Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit?

Checkout is at 10:00 AM.

Where is Riverside at Pear Tree Point Private Waterfront Escape with Hot Tub and Fire Pit located?

This family-friendly Chestertown holiday home is located on the waterfront, 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 Schooner Sultana. Larrabee Arts Center and Chestertown Farmers Market are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had the best time at this beautiful property. Killer views, great open floor plan and service with a smile. Very clean and exactly what we needed as a family! Great location with easy access to Washington College and Chestertown.
Stayed 2 nights in Sep 2026
Response from VrboOwner on 1 October 2026
Thank you so much, Lauren! We’re so glad your family enjoyed the house, the views, and the location. You were wonderful guests, and we’d be happy to host you again anytime you’re back in the Chestertown area!
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