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Stunning Home on a 25-Acre Private Woodland Estate

(18 Reviews)

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Last updated: 04/26/2017
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21 Unavailable
22 Today
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  • Minimum stay:2-3 nights
  • Sleeps:10
  • Bedrooms:4
  • Bathrooms:4.5
  • Property type:Estate
  • Internet:Yes
  • Pets considered:No
  • Wheel chair accessible:No

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.


Member since: 2014

Speaks: english, french
Response time: Within an hour
Response Rate: 100%
Calendar last updated: 04/26/2017

Property Type

  • Estate
  • 5500 sq. ft.

House Rules

  • Max. occupancy 10
  • Minimum Age Limit For Renters:

    Minimum age of primary renter is 25...moreless

  • Non Smoking Only:

    Smoking permitted in outdoor areas. Ashtrays must be used and provided by renters....moreless

  • Not Suitable For Children:

    Children under 10 years not permitted due to safety and security concerns....moreless

  • Pets Not Allowed

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Long-Term Renters Welcome
  • Wheelchair Inaccessible

Bedrooms: 4 Bedrooms, Sleeps 10, Beds for 8-10

  • Bedroom 1: 1 king

    Ensuite bathroom. Shared balcony....moreless

  • Bedroom 2: 1 queen

    Shared balcony; ensuite vanity and toilet...moreless

  • Bedroom 3: 1 double

    Ensuite vanity and toilet...moreless

  • Bedroom 4: 2 twin/ single

    On 4th floor. No bathroom on this level....moreless

  • Bedroom 5: 1 sleep sofa /futon

    Entertainment room/lower level. Doors for privacy. Bathroom....moreless

  • Master bedroom and Bedroom #2 share a balcony.

Bathrooms: 4 Bathrooms, 1 Half Bathroom

  • Bathroom 1: toilet

    Main floor powder room...moreless

  • Bathroom 2: toilet, tub, shower

    Ensuite Master Bedroom; large vanity....moreless

  • Bathroom 3: toilet, tub, shower

    Ensuite Bedroom #2. Shares'Jack & Jill'tub and shower w/BR#3...moreless

  • Bathroom 4: toilet, tub

    Ensuite Bedroom#3. Shares'Jack&Jill'tub & shower w/Bedroom#2...moreless

  • Bathroom 5: toilet, shower

    Spa area. Also serves as bathroom for entertainment room....moreless

  • 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....moreless

Other Amenities

  • 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....moreless


  • Satellite / Cable
  • Television:

    2 wifi comparable flat sceen tvs...moreless


  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Spa
  • Tourist Attractions


  • Churches
  • Festivals
  • Health/Beauty Spa
  • Live Theater
  • Marina
  • Museums
  • Restaurants
  • Ruins
  • Winery Tours

Local Services & Businesses

  • ATM/Bank
  • Fitness Center
  • Groceries
  • Hospital
  • Laundromat
  • Massage Therapist
  • Medical Services

Leisure Activities

  • Antiquing
  • Beachcombing
  • Bird Watching
  • Boating
  • Eco Tourism
  • Horseback Riding
  • Paddle Boating
  • Photography
  • Scenic Drives
  • Shelling
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing

Location Type

  • Resort:

    Highfield Manor includes an indoor sauna and eight-person jacuzzi. The property also offers an indoor Eternity Pool (available April-October)....moreless

  • Village:

    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

  • Water View:

    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

  • Waterfront:

    Enjoy floating on Whitehill Pond, or spend the day fishing. Wildlife lovers can view bald eagles, heron, hawks, pheasant, grouse and wild turkey. Foxes, beaver and deer are often observed....moreless

Sports & Adventure Activities

  • Cycling
  • Deepsea Fishing
  • Equestrian Events
  • Fishing
  • Freshwater Fishing
  • Golf
  • Hiking
  • Hunting
  • Jet Skiing
  • Kayaking
  • Sailing
  • Sound/Bay Fishing
  • Swimming
  • Water Skiing


  • Dining Area
  • Seating for 8 people


  • Air Conditioning
  • Clothes Dryer
  • Fireplace:

    Living room...moreless

  • Hair Dryer
  • Heating
  • Internet:

    2 Wifi compatable flat screen televisions...moreless

  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking:

    5-bay carport ...moreless

  • Towels Provided
  • Washing Machine
  • Wood Stove:

    Non-operative wood stoves are in all 3 bedrooms and lower-level entertainment room....moreless


  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen:

    Gourmet kitchen with granite countertops and island....moreless

  • Microwave
  • Oven:

    Double oven....moreless

  • Pantry Items:

    Basic spices, coffee filters, etc. Paper towels, napkins and dish towels included. Dish washing detergent and household cleaners included. ...moreless

  • Refrigerator:


  • Stove:

    Viking stove and Jenn-Air warmer. Also, outdoor propane grill on lower level deck....moreless

  • Toaster


  • Balcony:

    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

  • Deck / Patio:

    Umbrella/table for four. Additional deck seating for ten....moreless

  • Lawn / Garden
  • Outdoor Grill

Pool / Spa

  • Heated Pool
  • Hot Tub:

    Indoor, lower level spa. Eight-person capacity. Available year-round....moreless

  • Indoor Pool
  • Private Pool:

    Eternity indoor heated plunge pool on property. Pool is available from April through October....moreless



Write a review 4.8
from 18 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Holiday Wknd 2017
May 26 - May 29, 2017
3 night min stay
Labor Day Wknd 2017
Sep 1 - Sep 4, 2017
3 night min stay
Thanksgiving 2017
Nov 23 - Nov 26, 2017
3 night min stay
Christmas 2017
Dec 22 - Dec 26, 2017
3 night min stay
New Year's Eve 2017
Dec 29 - Jan 1, 2018
3 night min stay
Low Season
Jan 2 - Mar 29, 2018
2 night min stay
$1,999 $5,999
My Standard Rate
2 night min stay
$599 $699
Thu, Fri, Sat
$3,999 $8,999

Rates are based on 8 guests; add $50 per night, per additional guest

* Approximate Monthly rates, actual rate will depend on the days of the month you stay

Additional information about rental rates

Fees and Rental Conditions:

  • Cleaning Fee $100 + tax
  • Property Damage Protection $99
  • 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.

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Last updated: 04/26/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


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


Owner info

Contact us

Speaks: english, french
Response time: Within an hour
Response Rate: 100%
Calendar last updated: 04/26/2017

Send email

Links to more information:



  • Highfield Manor, Chestertown MD.

    Highfield Manor, Chestertown MD.

  • Whitehill Pond as viewed from stone terrace.

    Whitehill Pond as viewed from stone terrace.

  • Frog Pond entryway

    Frog Pond entryway

  • Entry foyer

    Entry foyer

  • Panoramic view from living area

    Panoramic view from living area

  • View from Living Room

    View from Living Room

  • Reading Area

    Reading Area

  • View from Living Room and Bedroom #1 and #2 Balconies

    View from Living Room and Bedroom #1 and #2 Balconies

  • Ensuite bathroom, Bedroom #1

    Ensuite bathroom, Bedroom #1

  • Bedroom #3, Full bed

    Bedroom #3, Full bed

  • View from Lower Level balcony

    View from Lower Level balcony

  • Sauna and eight-person Jacuzzi

    Sauna and eight-person Jacuzzi

  • Highfield Manor, Chestertown MD

    Highfield Manor, Chestertown MD

  • Whitehill Pond as seen from stone terraces

    Whitehill Pond as seen from stone terraces

  • Frog Pond patio

    Frog Pond patio

  • Living Room

    Living Room

  • Panoramic view from living area

    Panoramic view from living area

  • Dining Area

    Dining Area

  • Gourmet kitchen

    Gourmet kitchen

  • Bedroom#1, King bed

    Bedroom#1, King bed

  • Bedroom #2, Queen bed

    Bedroom #2, Queen bed

  • Tree-top 'bonus' bedroom, 2 twins, no bathroom on this level.

    Tree-top 'bonus' bedroom, 2 twins, no bathroom on this level.

  • Lower Level Entertainment Area, TV and Queen sleep sofa

    Lower Level Entertainment Area, TV and Queen sleep sofa

  • Pool House/Eternity Pool

    Pool House/Eternity Pool

VRBO #606821

This listing was first published here in 2014.

Date last modified - Wednesday, April 26, 2017

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