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Stunning Home on a 25-acre Private Woodland Estate

Bedrooms 4
Half Baths1
Space 510 m²
Property type estate
Minimum Stay 2 - 3 nights


About the property

Mid-Century Estate w/Pond, Indoor Pool, Spa/Sauna, Gourmet Kitchen, sleeps 8-10

Highfield Manor is the perfect location for your romantic wedding and reception, corporate event, or vacation with family and friends.

Nestled amongst towering great oaks and rushing streams, Highfield Manor offers guests luxurious living, breathtaking views of Whitehill Pond and a relaxing indoor pool and sauna....all just minutes from the Chesapeake Bay.

Our guests can enjoy al fresco dining on the many stone terraces and wrap-around balconies. Later, take a stroll along Whitehill pond, and enjoy its lovely fountain and wooden float. Hike across running streams via quaint wooden footbridges to explore the 25 acres of flora and fauna. Relax by the serene koi pond, with playful frogs and turtles, and a beautiful stone waterfall.

Once indoors, you'll be greeted with a stylish yet comfortable modern estate home. The living and dining areas are anchored by a large wood-burning fireplace. For the musician, an ebony baby grand piano sets off the unbelievable panoramic view of Whitehill Pond and beyond. Floor-to-ceiling windows create an atmosphere of living in the sky!

A mix of mid-century modern and circa-1930 French salon furniture nicely complement the original artwork and modern architectural details of the home.

Just ahead is every gourmand's dream; a custom kitchen featuring a Viking stove, double oven, Sub-Zero refrigerator, Jenn-Aire warmer, wet bar, granite countertops and a large butcher-block island. You can prepare an intimate dinner for two or a feast for many...Bon Appetit!

Next, walking up the open staircase, you'll discover the master bedroom, with king bed, built-in cabinets, ensuite bathroom and a balcony overlooking the property. The balcony is a perfect spot to enjoy your morning coffee or an evening cocktail.

Each tastefully decorated bedroom on this level has a wood-burning stove (non-operational) and plenty of storage.

Bedroom 2 also has a balcony and a queen bed, as well as an ensuite bathroom.

Bedroom 3 has a full bed and an ensuite bathroom.

Next, walk up the open staircase to the bonus bedroom, with treetop views, twin beds and cable/wifi flatscreen TV. This spot has been called the highest point in Kent County. What views!

Another fabulous feature of Highfield Manor is the indoor spa located on the lower level. Relax and de-stress in the built-in sauna and eight-person Jacuzzi. For your convenience, the spa area includes a large shower and powder room.

Once you leave the spa you can relax in the nicely appointed entertainment room, featuring a large flat-screen TV, queen sleep sofa, poker/backgammon table and walk-out deck.

Just steps away, Highfield Manor also includes a detached enclosed pool house featuring an Eternity Pool* and 5-bay carport.

Access to the pool and parking is included in your Highfield Manor rental.

Due to safety and security concerns, children under ten years old are not permitted at Highfield Manor. Events for more than 10 persons will incur an additional fee, and must be pre-arranged with and approved by the management.

Highfield Manor's unique architecture and natural setting is often compared to the modern classic estate Fallingwater. We hope you'll enjoy your stay, and choose to visit Highfield Manor time and again when on Maryland's beautiful Eastern Shore.

* The Eternity Pool is NOT AVAILABLE November-March. The Indoor Jacuzzi is available for your use during this period.

More Details

John Kardos
Member since: 2014
Speaks english, french
Response time:
Within an hour
Response rate:
Calendar last updated:
April 18, 2017


Accommodation and Amenities for this vacation estate rental in Chestertown, Maryland

Property Type:
  • estate
  • Guests provide their own meals
Floor Area:
  • 510 m²
House Rules:
  • Max. occupancy: 10
  • non smoking only ...
  • pets not allowed
  • children not allowed ...
  • Minimum Age Limit for Renters ...
Location Type:
  • Resort ...
  • Village ...
  • Water View ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Spa
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Fireplace ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Wood Stove ...
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 4 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , Main floor powder room
    Bathroom 2 - toilet , tub , shower , Ensuite Master Bedroom; large vanity.
    Bathroom 3 - toilet , tub , shower , Ensuite Bedroom #2. Shares'Jack & Jill'tub and shower w/BR#3
    Bathroom 4 - toilet , tub , Ensuite Bedroom#3. Shares'Jack&Jill'tub & shower w/Bedroom#2
    Bathroom 5 - toilet , shower , Spa area. Also serves as bathroom for entertainment room.
  • Bedrooms #2 and #3 have private vanities and toilets, but share a bathtub and shower (aka Jack & Jill bathroom). Secure doors throughout for complete privacy.
  • 4 Bedrooms, Sleeps 10
  • Bedroom 1 - 1 king , Ensuite bathroom. Shared balcony.
    Bedroom 2 - 1 queen , Shared balcony; ensuite vanity and toilet
    Bedroom 3 - 1 double , Ensuite vanity and toilet
    Bedroom 4 - 2 twin/ single , On 4th floor. No bathroom on this level.
    Bedroom 5 - 1 sleep sofa /futon , Entertainment room/lower level. Doors for privacy. Bathroom.
  • Master bedroom and Bedroom #2 share a balcony.
  • Satellite / Cable
  • Television ...
  • Balcony ...
  • Deck / Patio ...
  • Lawn / Garden
  • Outdoor Grill
  • long term renters welcome
  • wheelchair inaccessible
Pool / Spa:
  • Heated Pool
  • Hot Tub ...
  • Indoor Pool
  • Private Pool ...
  • Sauna ...
  • churches
  • festivals
  • health/beauty spa
  • live theater
  • marina
  • museums
  • restaurants
  • ruins
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • jet skiing
  • kayaking
  • sailing
  • sound/bay fishing
  • swimming
  • water skiing
Events requiring use of the property by more than 10 people are allowed but require an additional charge. Please contact owner for details. Due to safety and security concerns, children under ten years are not permitted. Pool is available April through October.


Nearest Airport
70 Miles
Baltimore Washington Int'l or Philadelphia Int'l
Nearest Barpub
4 Miles
JR's Pub
Nearest Ferry
69 Miles
Cape May-Lewes Ferry
Nearest Golf
4 Miles
Chester River Yacht and Country Club (private)
Nearest Train
55 Miles
Wilmington DE
Nearest Motorway
10 Miles
US 301
Nearest Restaurant
4 Miles
Lemon Leaf Cafe
Nearest Beach
8.5 Miles
Rock Hall MD
Car: recommended

Charming historic Chestertown MD houses Washington College as well as Emmanuel Church, which was the site of the first Episcopal Church in America. Many significant sites from America's Colonial Period, the Revolutionary War, War of 1812 and the Civil War are in the area.

Chestertown also hosts lively entertainment at The Garfield Theatre, and many festivals along the riverfront and at the town's Fountain Park. A replica of the 1768 schooner Sultana holds proud watch over the marina, and also offers educational tours.

The award-winning Lemon Leaf Cafe has the 'best cream of crab soup' on the Eastern shore, but don't leave town without trying their famous crab cakes and lemon meringue pie. Evening entertainment is often offered at the adjoining JR's Pub. One can spend the day shopping, antiquing or just strolling along the cobblestone sidewalks of this Eastern Shore gem.

Shopping in Chestertown can take you from the gorgeous antiques at Poor Richard's to the chic styles at Mimi's Closet. Don't miss the local flavor of gift shops Twigs and Teacups, Gabriela's or Dockside. Art galleries, coffee shops and quaint restaurants will entice you, and the weary can have a day of beauty at Flow salon. Also, the Queenstown Outlets are only 25 minutes away.

Just down the road is a boater's paradise. Rock Hall, Maryland is a waterfront town offering gorgeous views of America's treasure, the Chesapeake Bay. Swim, sail or kayak to your heart's content. Crabs, clams and rockfish are the prime catch for the local watermen, and their bounty can become your entree within just a few moments.


Rates & Availability

Rental Rates for this vacation estate rental in Chestertown, Maryland

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
Holiday Wknd 2017
May 26 2017 - May 29 2017
3 night minimum stay
Labor Day Wknd 2017
Sep 1 2017 - Sep 4 2017
3 night minimum stay
Thanksgiving 2017
Nov 23 2017 - Nov 26 2017
3 night minimum stay
Christmas 2017
Dec 22 2017 - Dec 26 2017
3 night minimum stay
New Year's Eve 2017
Dec 29 2017 - Jan 1 2018
3 night minimum stay
Low Season
Jan 2 2018 - Mar 29 2018
2 night minimum stay
My Standard Rate
2 night minimum stay
Notes: Rates are based on 8 guests; add C$68 per night, per additional guest

Additional information about rental rates

Cleaning Fee C$135.15 + Tax
Property Damage Protection C$133.8
Refundable Damage Deposit C$405.46
Tax Rate 8.0%

Additional fee for parties or events exceeding 10 persons. No pets. No smoking indoors. No children under 10 years. Renter is fully responsible for any property damage while renting property. Owner is not responsible for any personal injury of renters or their guests. The use of spa facilities, pool and pond by renters or any guests is at their own risk. Swim at your own risk! No lifeguard is on duty. Pool is available April through October.

Owner's Cancellation Policy

100% refund if canceled at least 90 days before arrival date.
Enter dates for accurate pricing
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