Deerpond Carriage House

about us

Deerpond Carriage House

You will be staying in a charming, waterfront, one-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 trailerable 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 just a few miles away and observe many different birds of prey in their natural habitat.

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 Regency Chesapeake Bay Resort or the Choptank 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. 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!

get in touch


5211 Brooks Road
Woolford, Maryland 21677
410-221-7840 (p)


9am-7pm, weekend and weekdays, 3-day minimum rental
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