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Waterfront "GLASS TREE HOUSE" with Private Pier in Chestertown

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vacation rental description

Come spend a long weekend, a week, or longer at the Glass Tree House--GET AWAY, RELAX, and commune with nature, family, friends.

Enjoy the house as a HUNTING LODGE during goose/duck/deer seasons, and a YACHTING PORT the rest of the year.

Unique, secluded, architecturally elegant, the 3-story "Glass Tree House" is located on wooded waterfront on the Quaker Neck side of East Langford Bay, which is a deepwater tributary of the Chester River and Chesapeake Bay, on Maryland's "Eastern Shore."

Seven miles of country road from historic Chestertown--the seat of Kent County and home of Washington College--the Glass Tree House is designed and furnished for relaxing, informal,  outdoor-indoor living in close touch with nature. It provides a rich experience of an extraordinarily beautiful natural setting.

Perfect for one or two-family vacations, reunions, retreats, other gatherings--or a romantic escape for two. Sleeps up to 12 persons in five bedrooms. Fully equipped.

A BOATERS' PARADISE for large and small boats, sail or power, kayaks and canoes. Ideal for waterskiing. A canoe comes with the house.

SWIMMING from the pier or the sandy, shallow toddlers' beach.

FISHING and CRABBING from the pier, your boat, or the house canoe.

Ground Floor has three bedrooms--two bunk rooms  (4 bunks in each bunk room) and a small bedroom with full (double) bed. Large bathroom with washer and dryer. (Youngsters love having their own world on this floor.) 

Second Floor has living room with woodstove and piano, dining room (large table seats 12) and an efficient well-equipped kitchen with dishwasher. SLIDEAWAY GLASS WALLS in both living and dining areas transform this entire second floor, in warm weather, into a wonderfully spacious 4-sided screened veranda, with a 2-person hammock, a one-person hammock swing, and magnificent water views.

Third Floor has two bedrooms with queen beds, connecting bath, and outdoor decks.  One of these bedrooms is air-conditioned. Each bedroom has a desk, for those who have to do some work or write a letter.

OUTDOOR SPACES include a roofed patio on the ground floor with fridge, charcoal grill, and picnic table; tree-shaded yard with hammock between two shade trees; a 6' wide deepwater pier (6' MLW at the outboard end, 4' MLW alongside); and a large parking area with basketball hoop.

The Glass Tree House is one-of-a-kind, perfectly sited in a uniquely beautiful, unspoiled natural setting. It provides a delightfully informal and relaxing experience of harmony with nature--a complete break from the fastlane buzz and glitz of modern living. No granite counters in the kitchen and no marble tile in the bathrooms--but many have fallen in love with the special magic of this place, over the years. And you, too, may be entranced by its elegant simplicity, its openness to the air,water, woods, and light.

NO BETTER PLACE to enjoy your family, your friends, yourself--and Maryland's Eastern Shore!

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Last modified on 06-18-2014 at 5:46 PM.

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Ben Hopkins

house rental amenities

Secluded and private. Set among tall trees on unspoiled natural waterfront.

Hi-speed broadband wi-fi internet anywhere in or near the house.

Windows, windows, views and more views--into the trees and over the water.

BOATING AND SWIMMING from your own private pier right in front of the house. A long stretch of open but protected water that is perfect for small sail and power boating--also for canoeing, kayaking, and waterskiing. Larger boats can tie up at the pier and voyage out to the magnificent Chester River and Chesapeake Bay.

6x90-FOOT PIER has 4' MLW alongside, with two tie-off pilings. Depth at the end of the pier is 6' MLW. Normal tide range is about two feet.

Shallow sandy wading beach next to the pier is perfect for toddlers. Also serves as a boat launching ramp (with 4wd towing vehicle).

Ground level covered patio with fridge, grill, and picnic table.

Large parking area with basketball hoop.

Cooling summer breezes off the water.

Two charming historic towns nearby--Chestertown and Rock Hall. Annapolis is an easy one-hour drive.


ONLY 2 hours from Philadelphia, Baltimore, and Washington DC.--1.5 hours from Wilmington, Delaware.

Casual, comfortable, convenient, relaxing.

activities and attractions in Chestertown Maryland

Ten minutes to historic Chestertown, with its charming 18th century atmosphere. It offers casual and fine dining, boutique and regular shopping, antiquing, movies, and the lovely campus of Washington College.

Drive 15 minutes to historic Rock Hall and Harbor on Chesapeake Bay--for restaurants, art galleries, seafood markets, boat charters, fishing excursions, and guided kayak tours. Drive an hour to Annapolis, the capitol of Maryland, and stroll/shop/dine along the docks of its colorful harbor.

(More info about all of these locations is available on their websites.)

vacation rental rates


Weekly (Fri-Fri):  1400 for one week, 1200/week for more than one week.

Three-day weekends:  1100 (additional days at 100)

LABOR DAY WEEKEND (3 days):  1200 (additional days at 100)


Please inquire about rates during this period.

Special rate for Hunting Season (November-December-January)

Last minute bargains are sometimes available.







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Ben Hopkins

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Top things to do in Chestertown
  • Stroll the town square and waterfront
  • View the campus of Washington College
  • Go horseback riding at a local stable
  • Enjoy a guided kayak tour out of nearby Rock Hall
  • Eat some seafood and take in a movie
Top things to do on a budget
  • SNOOZE in a hammock
  • SWIM--or sunbathe on the pier
  • GO FISHING or set a CRAB trap
  • PADDLE your own canoe
  • WALK a country lane
Top things to do with a family
  • Relax, tell stories, enjoy the water views--from a hammock!
  • Boating, kayaking, waterskiing, swimming, fishing, crabbing
  • Throw some b-ball hoops
  • Feast on local fish and crabs
  • Relax some more--in the hammocks

Ben Hopkins , owner

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Ben Hopkins

traveler reviews for this chestertown house rental

A great week at the Glass Tree House!

Review submitted: August 22, 2012   Date of arrival: July 13, 2012

The house is just as described. It sits on a beautiful portion of the Chester River with an average depth of 8-10'. We entertained a large group over the first weekend and found the kitchen to be well equipped and the covered patio large enough for everyone! Going thru the next week we were able to visit both Chestertown and Rock Hall both having interesting shops and restaurants. But the most amazing part of this house is definitely the moveable walls. It gives you the feel of open air without the bugs/rain. (0f course you do need to close them if it is blowing rain) Overall, I think this is a reasonably priced rental with all you need to enjoy a week on the river!

Recommended for: adventure seekers, families with young children, families with teenagers, pet-friendly, sight seeing

Owners response: A couple of refinements for this good review:

The Glass Tree House fronts on "East Langford Bay" which is a deep water, river-like tributary of the much larger Chester River.

The "moveable walls" around the second floor living-dining area are made of glass, thus they do not block the light or the view when they are closed.

Helpful votes: 7 / 9


Reviews are the subjective opinions of travelers and not of, Inc.

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Ben Hopkins

Chestertown vacation rental

This vacation rental has been listed since 07/8/2008.

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