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The B&B of Anchorage - Skipjack

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Exterior
Room
Interior
Bathroom
Skipjack room private balcony

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Private pool
  • Breakfast included
  • Onsite parking available
  • Free Wi-Fi
  • Deck or patio
  • Air-conditioning

Explore the area

View map
Trappe, MD
  • Place, Bill Burton Fishing Pier State Park
    ‪5 min drive‬
  • Place, Dorchester County Visitors Center
    ‪9 min drive‬
  • Place, Harriet Tubman Museum and Educational Center
    ‪10 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪30 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Skipjack

1 King Bed

1 bathroom, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet

Spaces

Deck or patio
Porch or lanai
Outdoor play area
Garden
Dining area
Price is avg per night

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About this property

The B&B of Anchorage - Skipjack

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.

House Rules

Check in after 3:00 PM
Check out before 11:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Gather used towels
Remove personal items and remove leftover food and drinks
Turn off the lights
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property # 1654200vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
This property uses some solar energy
Safety features at this property include a fire extinguisher, a smoke detector and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

Frequently asked questions

Does The B&B of Anchorage - Skipjack have a pool?

Yes, this property has an outdoor pool.

Is The B&B of Anchorage - Skipjack pet-friendly?

No, pets are not allowed at this property.

How much is parking at The B&B of Anchorage - Skipjack?

On-site parking is available at the property.

What time is check-in at The B&B of Anchorage - Skipjack?

Check-in begins at 3:00 PM.

What time is check-out at The B&B of Anchorage - Skipjack?

Checkout is at 11:00 AM.

Where is The B&B of Anchorage - Skipjack located?

Situated in Trappe, this bed & breakfast is 1.7 mi (2.8 km) from Bill Burton Fishing Pier State Park and within 6 miles (10 km) of Dorchester County Visitors Center and Ruark Boatworks. Dorchester General Hospital and Meredith House are also within 6 miles (10 km).

The B&B of Anchorage - Skipjack Reviews

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 10 out of 10 reviews
Rating 8 - Good. 0 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Sarah G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Donna B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anchorage - Skipjack

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!
Stayed 2 nights in Jun 2024
Verified

10/10 Excellent

Jerry K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

R & R

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.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Carolyn D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Oasis

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.
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Coryn V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 3 nights in Jun 2026
Verified

10/10 Excellent

Michael J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Highly recommend

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.
Stayed 2 nights in Sep 2022
Verified

10/10 Excellent

Patrick K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

2 days away!!

The property is awesome, right on the river! So relaxing. Woody and Michelle couldn't have made us feel more comfortable. Great stay!
Stayed 2 nights in Jun 2022
Verified

10/10 Excellent

Jon G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Little Bliss

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!
Stayed 3 nights in Jul 2021
Verified

10/10 Excellent

Jan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful getaway!

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.
Stayed 3 nights in May 2021
Verified

10/10 Excellent

Charlene R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Highly recommend the Anchorage B&B

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.
Stayed 2 nights in Aug 2020

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