The B&B of Anchorage - Skipjack

Trappe, Maryland
$299 avg/night Minimum Stay 2 Nights
Bed 1

Bed

Bath 1

Bath

Home Bed & Breakfast

Property Type

Sleep 2

Max Sleeps

Night 2 nights

Min Stay

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.>

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • MORE

    At Least 80% Lighting From LEDs Beach Towels Books Local Artist Showcase Smoke-free Property Vegan Dining Options Vegetarian Dining Options Desk Desk Chair Energy-saving Switches Iron/ironing Board Private Pool Recycling
  • OUTDOOR

    BBQ Grill(s) Firepit Garden Outdoor Furniture
  • INTERNET

    Available In All Rooms: Free WiFi Available In Some Public Areas: Internet Access
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycling Golfing Kayaking Outdoor Pool Playground
  • FOOD AND DRINK

    Free Breakfast Available Coffee/tea Maker Cookware/dishes/utensils Dining Table Ice Maker Paper Towels Refrigerator
  • GUEST SERVICES

    Change Of Towels (on Request)
  • FAMILY FRIENDLY

    Dining Table Outdoor Pool Playground Refrigerator
  • BEDROOM

    Air Conditioning Bed Sheets Heating
  • BATHROOM

    Hair Dryer Shampoo Shower Soap Toilet Paper Towels
  • OUTDOOR SPACE

    Deck Or Patio

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 2

Map Map

School District Rates & Availability

Review Review

  • Sarah G.

    Submitted Sep 26, 2025

    Stayed Sep 18, 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!!

  • Donna B.

    Submitted Jun 12, 2024

    Stayed Jun 8, 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!

  • Carolyn D.

    Submitted May 8, 2024

    Stayed May 3, 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.

  • Jerry K.

    Submitted Oct 6, 2023

    Stayed Sep 29, 2023

    A really good stay, spacious, clean room, beautiful grounds for relaxing by the water or lying in the hammock under the trees. Michelle and Woody made us feel welcome and comfortable. Woody gives helpful tourist suggestions and also makes delicious breakfasts, which are included. We would plan to return for future events in the area and also just to stay at the B & B for R & R.

  • Michael J.

    Submitted Sep 25, 2022

    Stayed Sep 23, 2022

    I booked this place for the weekend to celebrate my wife's birthday. Our hosts, Woody & Michelle, couldn't have been nicer or more accommodating. They helped us decide what things to see during our visit, and all of their suggestions were excellent. They breakfasts they served were delicious. Their place is on a beautiful piece of land with great waterfront views. The room was nice and clean with a nice shower and plush towels. If you are looking for a great getaway that is fairly close to a number of fun activities, I highly recommend the Anchorage 1800.

  • Patrick K.

    Submitted Jun 20, 2022

    Stayed Jun 15, 2022

    The property is awesome, right on the river! So relaxing. Woody and Michelle couldn't have made us feel more comfortable. Great stay!

  • Jon G.

    Submitted Jul 8, 2021

    Stayed Jul 5, 2021

    We enjoyed a thoroughly relaxing stay at the Anchorage. When we were finished touring both new and familiar destinations along the Eastern Shore, the Anchorage’s river-front beach and pool area offered perfect spots to while away the hours. What’s more, Michelle and Woody are truly affable and capable hosts. Kudos and thanks for such a beautiful property and welcoming atmosphere!

  • Jan S.

    Submitted May 24, 2021

    Stayed May 21, 2021

    Michelle and Woody are consummate hosts! They made sure we had everything we needed, from delicious breakfasts to local knowledge to onsite entertainment. The rooms are even more comfortably equipped than described, the property is beautiful, and the atmosphere relaxing. We kayaked, lazed in hammocks, watched birds and rabbits, and enjoyed the river views. Trips to Cambridge and Easton resulted in great meals and sight-seeing. We look forward to visiting again and sharing this Eastern Shore gem with our friends.

  • Charlene R.

    Submitted Aug 27, 2020

    Stayed Aug 22, 2020

    We absolutely loved our stay at the Anchorage. We stayed in the Skipjack room. The owners did everything they could to make our stay as enjoyable as possible. The food was excellent, million dollar views, the property is gorgeous, the pool area is well maintained and the old smokers lounge was a very nice touch. I was expecting a mini fridge and a little table a chairs in the room, but the owners were gracious enough to allow us to use their refrigerator/freezer for our needs and we enjoyed eating meals at the beautiful outside table next to the pool covered by a pergola, with views of the ocean, so we really didn't miss out on anything. Our visit was a Birthday gift for my boyfriend, and the owners even went the extra mile and added birthday candles to a World Famous (right Woddy ;-)) homemade blueberry cornbread (which was amazing), they made for us on the last day of our stay. All the extra little touches they did made this trip so much more memorable. The location is great if you want to explore little towns like Cambridge, St. Michael's and Tilghman Island. We did not utilize the kayaks, but that is on our list of to dos during our next visit to the Anchorage. By far, the best B&B I have stayed at.

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Total

Includes taxes and fees
$299+
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