Stunning Home on a 25-Acre Private Woodland Estate(18 Reviews)
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- Minimum stay:2 nights
- Property type:Estate
- Pets considered:No
- Wheel chair accessible:No
About the Property
Mid-Century Estate w/Pond, Indoor Pool, Spa/Sauna, Gourmet Kitchen, sleeps 8-10
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.
Member since: 2014
- 5500 sq. ft.
- Vacation Rental
- Guests Provide Their Own Meals
- Long-Term Renters Welcome
- Minimum Age Limit For Renters:
- Non Smoking Only:
- Not Suitable For Children:
- Pets Not Allowed
- Wheelchair Inaccessible
Bedrooms: 4 Bedrooms, Sleeps 10, Beds for 8-10
- Master bedroom and Bedroom #2 share a balcony.
Bathrooms: 4 Bathrooms, 1 Half Bathroom
- Away From It All
- Tourist Attractions
- Health/Beauty Spa
- Live Theater
- Winery Tours
Local Services & Businesses
- Fitness Center
- Massage Therapist
- Medical Services
- Bird Watching
- Eco Tourism
- Horseback Riding
- Paddle Boating
- Scenic Drives
- Sight Seeing
- Wildlife Viewing
Historic Chestertown is the home of Washington College and it's many events. Fountain Park hosts concerts, festivals and a weekly Farmer's Market. Visit the award-winning Lemon Leaf Cafe & JR's Pub....moreless
Lovely fountain views of Whitehill Pond as well as streams and footbridges from the floor-to-ceiling windows, balconies or stone terraces. Relax at the serene koi pond with its stone waterfall....moreless
Sports & Adventure Activities
- Deepsea Fishing
- Equestrian Events
- Freshwater Fishing
- Jet Skiing
- Sound/Bay Fishing
- Water Skiing
- Coffee Maker
- Dishes & Utensils
- Pantry Items:
Balconies off of the second level bedrooms and lower level entertainment room provide gorgeous views of Whitehill Pond and the surrounding streams, footbridges and woodlands. Seating areas included....moreless
- Lawn / Garden
- Outdoor Grill
|Dates||Nightly||Weekend Night||Weekly||Monthly *||Event|
My Standard Rate
2 night min stay
Thu, Fri, Sat
Rates are based on 8 guests; add $100 per night, per additional guest
Additional information about rental rates
Fees and Rental Conditions:
- Property Damage Protection $99
- Cleaning Fee $100 + tax
- Refundable Damage Deposit $300
- Tax Rate 8%
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.
Don't forget your vacation protection! Get protected now
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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.
Highfield Manor, Chestertown MD.
Whitehill Pond as viewed from stone terrace.
Frog Pond entryway
Panoramic view from living area
View from Living Room
View from Living Room and Bedroom #1 and #2 Balconies
Ensuite bathroom, Bedroom #1
Bedroom #3, Full bed
View from Lower Level balcony
Sauna and eight-person Jacuzzi
Highfield Manor, Chestertown MD
Whitehill Pond as seen from stone terraces
Frog Pond patio
Panoramic view from living area
Bedroom#1, King bed
Bedroom #2, Queen bed
Tree-top 'bonus' bedroom, 2 twins, no bathroom on this level.
Lower Level Entertainment Area, TV and Queen sleep sofa
Pool House/Eternity Pool
This listing was first published here in 2014.
Date last modified - Sunday, February 19, 2017
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