Bed and Breakfast in Maryland
2 guests · 1 bedroom · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this bed and breakfast
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal Telescopic Tidewater Style Bed & Breakfast called The Anchorage, circa 1800 facing the Choptank River. There are also 3 other rooms available at the B&B if traveling in groups or with family members. We are located right outside the historical town of Trappe very close to Easton, Oxford, Cambridge, and St. Michaels. Rooms include a daily continental breakfast.
Amenities
Non-smoking
No pets allowed
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Jun 2026
We stayed here for Eagleman Ironman 70.3 and had such a wonderful experience. The property itself is absolutely beautiful — peaceful, tranquil, and the perfect place to relax and recharge during a busy race weekend. The setting felt calm and welcoming from the moment we arrived.Our room was very comfortable, spacious, and exceptionally clean. We appreciated having plenty of room for all of our race gear, which made a huge difference during an event weekend. The breakfast was also very good and a great added touch to our stay.I stayed with my husband, and my dad and brother also stayed at the property, and everyone enjoyed their experience. Whether you’re visiting for Ironman weekend or simply looking for a relaxing getaway, this is a place we would happily recommend and would absolutely stay at again
10 / 10Outstanding·Sep 2025
Our room was incredible and the property just outstanding! Such a beautiful location close to amazing restaurants! Woody and Michelle make an amazing breakfast and their hospitality made this experience absolutely perfect! We will be back...many times!!
10 / 10Outstanding·Jun 2024
What a delightful B&B. Clean, wonderful location. Owners could not be more inviting and the breakfast was absoluty delicious.
Thank you Michelle and Woody!
10 / 10Outstanding·May 2024
Partner and I wanted a nice place to stay that was close to Cambridge. We participated in a long bike ride the first morning and wanted to be able to relax the rest of the day. The Skipjack was perfect. Michelle and Woody were great hosts. We arrived late and Michelle made sure we knew exactly where we were going and has easy access once we arrived. They even included silverware and bowls since we needed our own breakfast early on Saturday. Bed was soft and cozy. Shower had great pressure and temp. Places to do work (though as description says no wifi out in the skipjack so we were prepared). It was rainy when we were there, but took a lovely walk to the water. Excited to return when the weather is better. It seems like a great place to go with multiple couples or families and everyone rents out a different place on the property.
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Top rated by guests
10Outstanding
(10 Ratings)
"We stayed here for Eagleman Ironman 70.3 and had such a wonderful experience. The property itself is absolutely beautiful — peaceful, tranquil, and the perfect place to relax and recharge during a bus..."
Coryn V.Don't miss out! Price and availability may change
