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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Quiet Waterfront Retreat in Estate Setting

Bedrooms 1
Space 750 sq. ft.
Property type cottage
Minimum Stay 3 nights


About the property

Cottage, 1 Bedroom, 1 Bath, (Sleeps 2)

Your hosts invite you to enjoy a visit to the land that James Michener wrote about in his book 'Chesapeake.' And remember to keep this visit a secret '...lest you awaken the rest of the world as to what a sequestered paradise this place is on the Eastern Shore.' (James Michener)

You will be staying in a charming, waterfront, 1-bedroom, carriage house located on a five-acre estate with surrounding tall pines and stately cedars. Your living quarters on the second floor, with private entrance and balcony, will overlook the pool and English garden below. Queen-size bed with down comforter and memory foam mattress, terry robes, overstuffed seating, comfortable antique furniture, and rich oak floors all add to a romantic and homelike ambiance. If you become chilled, just flip on the gas fireplace. Enjoy peace and quiet, observe wildlife, watch the sunrise from the beach, and sip a glass of wine on the dock or by the flagpole just before sunset.

With flat, traffic free roads and spectacular Chesapeake scenery, the area around Deerpond is noted for cyclists of all ages and abilities at any time of the year. Ride the same scenic roads where top triathletes compete in the summer months. You are likely to see many waterfront views with bald eagles, osprey and Canada geese (in the winter) soaring over your head as you ride or walk. Our property backs on Fishing Creek with miles of pristine shoreline - great for rowing or kayaking. If you have a trailer able boat, there is a free public launch ramp a couple miles away that you can use to launch it and bring it over to our dock. Have a bigger boat? Sail it in from the Bay which is just a few miles away -- there is deep water all the way. Don't have a boat? Got that covered too, we provide a tandem kayak and rowboat on the property for your use. Visit Blackwater National Wildlife Refuge to observe many different birds of prey in their natural habitat & the adjacent Harriet Tubman Underground Railroad Visitor Center to learn about the early history of this amazing woman. Oh - And don’t forget to bring a camera because every bend in the road can yield that nature picture of a lifetime. Drive into Cambridge to take in the many antique stores, play a round of golf at the Hyatt Resort and Country Club, or eat dinner at any of the fine restaurants in the area. Better yet, sample some of the famous Maryland crab cakes and bay oysters at one of the local restaurants near Deerpond.

If you want to come by boat, we have a deep water mooring for guests (7-9 ft) and can provide deep water dock access (5-6 ft depth) by special arrangement. This is very rare for the Eastern Shore.

Relaxation for you can take the form of just reading a book by the fire or listening to the sounds of nature. Many guests have commented on the extreme quiet that they experience staying at Deerpond. In many ways that alone is worth the price of admission. If sightseeing is your preference, view our list of day trips to take by car. Want to remain local then access the web link <<>> to get some ideas. Here are some guest book comments from the many folks that have stayed at Deerpond over the years:

“The best mini-vacation ever “--“This place is amazing”--“just like an Inn without any other guests”--“with thanks for your warm hospitality'--“a piece of heaven'--“Deerpond was all & more than we expected”--“wonderfully peaceful and relaxing”--“what a wonderful place for a romantic getaway”--“lovely, serene holiday”--“one week was not nearly enough time”--“the cottage was perfect”--“the views are spectacular”--“a perfect, quiet setting to work on our project”--“loved the kayak, pool and day trips”--”We don’t know how Deerpond could be any better” …

There are a hundred more of these in our guestbook; so, we invite you to come, read them yourself and experience Deerpond!

Places to go & things to do

Day 1 – Visit Oxford & St Michaels bayside towns – 1 hr. drive

Day 2 – Visit Ocean City beach &/or Assateague National Seashore beach, MD – 1 ½ hr drive

Day 2 (Alternative) – Visit to Chincoteaque & Assateaque National Seashore Park beach, VA – 2 hr drive

Day 3 – Visit Salisbury Zoo & Salisbury shopping mall – 1 hr drive

Day 4 – Visit Annapolis / Queenstown outlet shopping, MD – 1 ¼ hr drive

Day 5 – Golf Day (choice of 3 courses) and/or Spa @ Hyatt – ½ to 1 hr drive

Day 6 – Tour Blackwater Wildlife Refuge National Park / New! Harriet Tubman Underground Railroad - Visitor Center / kayaking / cycling / local sightseeing – ½ hr drive

Key words: Carriage House, waterfront vacation rental

More Details

Member since: 2005
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
April 29, 2017

About Bob

Unlike many other properties where you are given a set of keys and a phone number to call, your hosts live on the property in the separate manor house, friendly and available to answer all your questions and give their recommendations for restaurants, things to see and possible places to go during your pleasurable stay at Deerpond.

Bob purchased this cottage in 1997

Why Bob chose Maryland

The waterfront setting with acres of land and a $million backyard.

What makes this cottage unique

The waterfront setting changes by the minute as birds come and go, squirrels and rabbits play on the lawns, deer graze on the grasses (and sometimes the plants –which is not a good thing) and boats pass in the distance. It’s like living in a game reserve by the water. Then there is the peaceful quiet at night with almost none of the man-made sounds. You sleep like you never slept before.


Woolford Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Catering available
  • Lunch - Booking Possible
  • Dinner - Booking Possible
Floor Area:
  • 750 sq. ft.
House Rules:
  • Max. occupancy: 2
  • non smoking only
  • pets not allowed
  • not suitable for children
  • Minimum Age Limit for Renters ...
Location Type:
  • Beach View
  • Water View
  • Waterfront
  • Away From It All
  • Romantic
  • Air Conditioning ...
  • Broadband Access ...
  • Clothes Dryer ...
  • Gas Fireplace ...
  • Heating ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking Off Street ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Coffee Maker
  • Cooking Utensils ...
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 2 people
  • 1 Bathroom
  • Bathroom 1 -
  • Oak floor, vanity sink, full size tub/shower
  • 1 Bedroom, Sleeps 2
  • (1) Queen size Bed with High tech memory foam mattress pad for your sleeping pleasure.
  • Books
  • CD Player
  • DVD Player ...
  • Games ...
  • Satellite / Cable ...
  • Television ...
  • Video Library
  • Balcony ...
  • Boat ...
  • Deck / Patio
  • Gazebo ...
  • Kayak / Canoe ...
  • Lanai / Gazebo ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • wheelchair inaccessible
Pool / Spa:
  • Private Pool ...
  • churches
  • museums
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • boating
  • eco tourism
  • photography
  • shopping
  • walking
  • wildlife viewing
Sports & Adventure Activities:
  • cycling
  • fishing
  • fly fishing
  • golf
  • hunting
  • kayaking
  • pier fishing
  • swimming
Beach, Fishing peer, In-ground Pool (shared), balcony, DirecTV, Gas Grill - BBQ (shared), 2-person kayak, rowboat


Wonderful! 4.9/5 -
(59 traveler reviews)

Quiet Waterfront Retreat in Estate Setting
average rating of 4.915254 based on 59 reviews

Deer pond retreat

  • 5 of 5

We had a wonderful and relaxing stay at this beautiful home. Our hosts were gracious and friendly. We enjoyed special treats prepared by Cathy. Bob took time to point out points of interest and dining opportunities. We were able to enjoy the rich history of the area as well as seeing beautiful scenery. We would look forward to another visit in the fall.

  • Submitted: Apr 26, 2017
  • Stayed: Apr 2017
  • Source: VRBO, from HomeAway
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Washington, DC

Restful escape on Maryland's eastern shore

  • 5 of 5

We had a wonderful 4 days in a beautiful location on the eastern shore. This was our 4th time staying there & now we have been there in every season. The carriage house is maintained in beautiful condition, with attention given to every detail to make for either a quiet escape from busy city life or a place to relax while enjoying local attractions, such as Blackwater National Wildlife Refuge. The owners have thought of everything and go out of their way to make you feel welcome and special. We highly recommend it!

  • Submitted: Feb 1, 2017
  • Stayed: Jan 2017
  • Source: VRBO, from HomeAway
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Restful, relaxing rejuvenating location. .

  • 5 of 5

Bob and Cathy are amazing hosts who unobtrusively exceeded our expectations! We were able to disconnect with the world and its stresses and marvel in creation all around us. We were able to find refreshment for our mind, body and soul.

  • Submitted: Nov 13, 2016
  • Stayed: Nov 2016
  • Source: HomeAway
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Dayton, OH

Great views

  • 4 of 5

Walking down Brooks Road in the sunshine is a delight. Walking out the dock to watch a breeze pump some waves on the very shallow Fishing River tributary to the Chesapeake is a treat. Bob and Cathy are welcoming hosts to a beautiful loft with a sunrise and the water. Very comfy and well-designed space. It even has an adjustable shower that passes my 6'5" test.The refrigerator not so much for this foodie. And Lindy's Seafood is just around the country corner. The wifi is limited to Verizon digital. We had business demands that ate up capacity quickly.

We will be back, in the sailing season next time.

  • Submitted: Nov 4, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Sorry about the measured internet; but, cellular broadband is all that is available to us on the two mile peninsula that we live on.
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GREAT home away from home

  • 5 of 5

This is such a lovely place to stay! It's like being at home: clean, comfortable, and cozy! It's beautifully decorated, private, has all the conveniences of home, and is located in a beautiful area. Bob and Cathy are lovely people and make a great team - he makes the communication process easy, and she makes the unexpected but much-appreciated tasty treats! 😀򐀠Deer Pond is a little off the beaten path - which we really like - and a wonderful spot from which to explore the surrounding islands and small towns. If we come back to the area again, we'll wanna stay here. We're spoiled! Thanks so much!!

  • Submitted: Oct 20, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Glad you enjoyed your stay. The "Bob & Cathy Team" aim to please!
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Washington, DC

We had a wonderful time relaxing in the peaceful environment of Deerpond.

  • 5 of 5

It was our third time at Deerpond and every time there was been great! Cathy and Bob keep the property in wonderful shape. We really appreciate their hospitality, including sweet treats left on the steps for us to enjoy! It's a great place to sit and watch nature and it is close to Blackwater refuge, which is different every time we visit. We definitely want to come back!

  • Submitted: Oct 17, 2016
  • Stayed: Oct 2016
  • Source: HomeAway
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Nearest Airport
85 Miles
Baltimore International (BWI) (1 hr 40 mins)
Nearest Golf
15 Miles
Hyatt Chesapeake Bay
Nearest Motorway
15 Miles
State Hwy Route 50
Nearest Restaurant
7 Miles
Palm Beach Willies (15 minutes)
Nearest Beach
100 Miles
Ocean City (1hr 30 mins)
Car: necessary

Bird watching from your balcony. Finest Cycling in the mid-Atlantic region. Ironman course passes by the foot of our street.


Rates & Availability

Woolford Cottage Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
My Standard Rate Spring 2017
Jan 1 2017 - May 25 2017
3 night minimum stay
Summer Season 2017
May 26 2017 - Oct 4 2017
3 night minimum stay
Ironman Cambridge
Oct 5 2017 - Oct 8 2017
3 night minimum stay
My Standard Rate Fall 2017
Oct 9 2017 - Dec 31 2017
3 night minimum stay
My Standard Rate
3 night minimum stay

Additional information about rental rates

Cleaning $60 + Tax
Refundable damage deposit $100
Tax Rate 6.0%

Cancellation (30) days before, full refund less $15 processing fee
Cancellation within (30) days of arrival, no refund
Set of stairs leading the 2nd floor. Not wheel chair accessable.

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.

Enter dates for accurate pricing

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