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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

Stunning Home on a 25-acre Private Woodland Estate

Bedrooms 4
Separate WC's1
Space 5,500 sq. ft.
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:
18 April, 2017


Accommodation and facilities for this holiday estate in Chestertown in Pomona

Property Type:
  • estate
  • Self-catering
Floor Area:
  • 5500 sq. ft.
House Rules:
  • Max. occupancy: 10
  • non smoking only ...
  • pets not allowed
  • not suitable for children ...
  • 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 ...
  • Hob ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 4 Bathrooms
  • 1 Separate WC
  • Bathroom 1 - Toilet , Main floor powder room
    Bathroom 2 - Toilet , Bath (no shower) , Shower Enclosure , Ensuite Master Bedroom; large vanity.
    Bathroom 3 - Toilet , Bath (no shower) , Shower Enclosure , Ensuite Bedroom #2. Shares'Jack & Jill'tub and shower w/BR#3
    Bathroom 4 - Toilet , Bath (no shower) , Ensuite Bedroom#3. Shares'Jack&Jill'tub & shower w/Bedroom#2
    Bathroom 5 - Toilet , Shower Enclosure , 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 Extra Lg. Double Bed , Ensuite bathroom. Shared balcony.
    Bedroom 2 - 1 Large Double Bed , Shared balcony; ensuite vanity and toilet
    Bedroom 3 - 1 Double Bed , Ensuite vanity and toilet
    Bedroom 4 - 2 Single Bed , On 4th floor. No bathroom on this level.
    Bedroom 5 - 1 Sofa bed/Futon , Entertainment room/lower level. Doors for privacy. Bathroom.
  • Master bedroom and Bedroom #2 share a balcony.
  • Satellite / Cable
  • Television ...
  • Balcony ...
  • Terrace ...
  • Garden
  • Barbecue
  • Long-term Renters Welcome
  • wheelchair inaccessible
Pool / Spa:
  • Heated Pool
  • Hot Tub ...
  • Indoor Pool
  • Private Pool ...
  • Sauna ...
  • churches
  • festivals
  • Health/Beauty Spa
  • live theatre
  • marina
  • museums
  • restaurants
  • ruins
  • winery tours
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • Boating
  • eco tourism
  • horse riding
  • paddle boating
  • photography
  • scenic drives
  • Shelling
  • Shopping
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • jet skiing
  • Kayaking
  • sailing
  • 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.


Wonderful! 4.8/5 -
(18 traveller reviews)

Stunning Home on a 25-acre Private Woodland Estate
average rating of 4.7777777 based on 18 reviews

Perfect weekend for a graduation!!!

  • 5 of 5

We rented this beautiful home for our son's graduation from Washington College. John met us at the house at our convenience when we arrived in Chestertown and gave us a tour of his fabulous home. He was so warm and gracious. He thought of absolutely everything to make our stay a memorable one. I love to cook and the kitchen was an absolute dream with everything I needed to make our son's graduation weekend a real treat. Some of the people who live in Chestertown were just floored by this beautiful property. With the limited availability of hotel rooms available during graduation time, this was such gem!! Would love to return to this house with friends for a fun week, even without my son being at the college!! Just the best!! Thank you John for such great memories!!

  • Review Submitted: Jun 24, 2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
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Lovely Home and an Excellent Host!

  • 5 of 5

Highfield Manor is even more beautiful than the pictures imply, and John was a perfect host. Perfect place for a weekend getaway.

  • Review Submitted: May 16, 2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
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Perfect wedding

  • 5 of 5

We just got married at Highfield Manor and it was perfect. The property is amazing and the owner was warm, accommodating and helpful the during the planning and execution of the event. We and our guests had a wonderful day, and staying in the lovely house was just the icing on the cake. It's an amazing home, immaculately restored and decorated. Jack has thought of everything, including a sauna and lap pool! We're looking forward to staying again some day, just the two of us, and enjoying the serenity.

  • Review Submitted: Oct 13, 2015
  • Date of Stay: Oct 2015
  • Source: HomeAway
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Great stay!

  • 5 of 5

We had a party of 10 and really enjoyed our two night stay. The house was very beautiful, clean and equipped with everything we needed. The pool was a little smaller than we expected, but no complaints. It was very easy to get to and in a quiet, secluded area. It was only about 10 minutes from the bay. I would recommend this property for bachelor parties or any other large groups!

  • Review Submitted: Aug 25, 2015
  • Date of Stay: Aug 2015
  • Source: VRBO, from HomeAway
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Perfect Property

  • 5 of 5

The house is gorgeous and the property is perfect. A must stay!

  • Review Submitted: Aug 17, 2015
  • Date of Stay: Aug 2015
  • Source: VRBO, from HomeAway
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Annapolis, MD

Incredible home in a beautiful place

  • 5 of 5

Everything about this property was above and beyond. The house was spotless and offers so much more than just a place to sleep. The attention to detail was obvious from the excellent décor to the bath robes available in every room. Our group had everything we could have needed for the weekend and then some. The amenities and details of the house are only a part of what makes this property special. The grounds of the estate are absolutely stunning. We spent most of our time outside enjoying the views from many decks and patios, as well as wandering throughout the property. The owner went out of his way to allow me early access to the house, even showing up personally to let me in and show me around. Could not have asked for a better stay.

  • Review Submitted: Aug 6, 2015
  • Date of Stay: Jul 2015
  • Source: VRBO, from HomeAway
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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.


Prices & Availability

Prices for this holiday estate in Chestertown, Maryland

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Holiday Wknd 2017
26 May 2017 - 29 May 2017
3 night minimum stay
for 3 nights
Labor Day Wknd 2017
1 Sep 2017 - 4 Sep 2017
3 night minimum stay
for 3 nights
Thanksgiving 2017
23 Nov 2017 - 26 Nov 2017
3 night minimum stay
for 3 nights
Christmas 2017
22 Dec 2017 - 26 Dec 2017
3 night minimum stay
for 3 nights
New Year's Eve 2017
29 Dec 2017 - 1 Jan 2018
3 night minimum stay
for 3 nights
Low Season
2 Jan 2018 - 29 Mar 2018
2 night minimum stay
for 2 nights
My Standard Rate
2 night minimum stay
for 2 nights
Notes: Rates are based on 8 guests; add £42 per night, per additional guest

Additional pricing information

Cleaning Fee £78.23 + Tax
Property Damage Protection £77.44
Refundable Damage Deposit £234.68
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 for cancellations more than 90 days before check-in date.
Enter dates for accurate pricing
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Partner Offers

Portable wifi hotspot

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