Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon

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:
21 July, 2018

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 Woolford

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.


Accommodation and facilities for this holiday cottage rental in Woolford

Property Type:
  • cottage
  • Catering available
  • Lunch - Booking Possible
  • Dinner - Booking Possible
Floor Area:
  • 750 sq ft
House Rules:
  • Max. occupancy: 2
  • Minimum Age Limit for Renters ...
  • not suitable for children
  • pets not allowed
  • non smoking only
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:
  • antique hunting
  • 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 -
(78 traveller reviews)

94% Complete
2% Complete
1% Complete
1% Complete
0% Complete
Quiet Waterfront Retreat in Estate Setting
average rating of 4.9102564 based on 78 reviews

Fantastic Eastern Shore Getaway

  • 5 of 5

My wife and I had a wonderful three days at Deerpond. The Carriage House was the perfect retreat after we explored the beauty, nature and history of Dorchester County and beyond. The apartment was comfortable, quiet and well appointed. We were totally relaxed each evening sitting on the balcony sipping wine and enjoying the views of Fishing Creek and the pool and gardens below. Lots to see and do and all within an easy drive. Toured St. Michaels, Easton, Cambridge and the Wildlife Preserve nearby. Took in the brand new Harriett Tubbman museum and even drove the 1 1/2 hours to Chincateague Island Virgina to see the wild ponies. That is definately worth the trip. Bob and Kathy were great hosts and we highly recommend the Carriage House and Deerpond.

  • Review Submitted: 03/05/2017
  • Date of Stay: April 2017
  • Source: VRBO, from HomeAway
Owner's Response: Very happy to hear that you enjoyed your stay with us. Especially noteworthy is your trip to Chincateague Island which we highly recommend to all our visitors. If you like long sandy white beaches and a great visitors center, it is one of the most beautiful seashore settings in the Midlantic area.
Did you find this review helpful?
0 0
Jersey City, NJ

Peaceful Retreat

  • 5 of 5

Wonderful but brief stay in the carriage house. It was well appointed, comfortable and totally relaxing. The grounds are beautifully done and worth exploring. Our hosts are hospitable and very easy going. Definitely worth a return trip.

  • Review Submitted: 11/07/2018
  • Date of Stay: July 2018
  • Source: HomeAway
Did you find this review helpful?
0 0

Lovely setting. Pool was great on blistering hot days. Clean and comfortable accommodations

  • 5 of 5

The VRBO is a large space above the garage but it feels comfortable and not at all a “converted space”. It all sits on a large space on Fishing Creek and the view is gorgeous. The owners are very nice and thoughtful. We would definitely go again. It is FAR from real food so plan ahead and bring food along. We got things on the way but it would have been better if we had planned a bit

  • Review Submitted: 06/07/2018
  • Date of Stay: June 2018
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0
Maplewood, NJ

The perfect Eastern Shore experience

  • 5 of 5

Bob's place was perfect for our anniversary getaway. The apartment is tastefully furnished, impeccably clean, and has everything needed for an extended stay. It is the perfect Eastern Shore experience. It feels very remote, with plenty of quiet, yet it is less than 20 minutes from downtown Cambridge. The access to the pool, dock, kayak/canoe, and waterside Adirondack chairs makes a stay here very luxurious and just what we were hoping to get out of our stay in the area. Bob and Cathy were incredibly welcoming and helpful with information. They definitely go above and beyond to make their guests' stay as comfortable and enjoyable as possible. We recommend staying here wholeheartedly!

  • Review Submitted: 24/06/2018
  • Date of Stay: June 2018
  • Source: HomeAway
Owner's Response: We have never had such well organized guests. They only stayed 3 nights but managed to visit 5 days worth of places to go. Congratulations on the anniversary. Just in case anyone else wants to celebrate their anniversary, I think they dined at the Bistro in Cambridge (French), the number one restaurant in town.
Did you find this review helpful?
0 0
Denton, Texas

Wonderful place! You will enjoy it!

  • 5 of 5

This was a beautiful and relaxing get away! Highly recommended. The location is literally at the end of a long peninsula, so there is no traffic on the road. The grounds are gorgeous, as is the view of the Chesapeake. The carriage house apartment was very comfortable with a good bed and everything you need. The shower was great, and the kitchen well equipped. We were able to stream Netflix through our phone via a hotspot using Verizon - strong signal.

Cathy was out of town, but Bob was a warm and welcoming host, and we enjoyed visiting with him. No reservations about recommending Deer Pond. If on the Eastern Shore, this is probably the best place you will find.

  • Review Submitted: 25/05/2018
  • Date of Stay: May 2018
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Nice property but we were rained out.

  • 3 of 5

The property is accurately reflected in the posting, the grounds are picturesque and the efficiency well maintained and furnished. The hosts were gracious and allowed privacy. Unfortunately, we were rained out, several inches over a four day period, and left a day early.

  • Review Submitted: 19/05/2018
  • Date of Stay: May 2018
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0


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

Contact Owner

Additional information about rental rates

Cleaning Fee AU$80.88
Refundable Damage Deposit AU$134.8

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 cancelled at least 30 days before arrival date.

Other Holiday Properties