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5 bedroom Bed and Breakfast on the Choptank River

Photo gallery for 5 bedroom Bed and Breakfast on the Choptank River

Room
Dining
Bathroom
Bathroom
Private kitchen

Reviews

10 out of 10

Exceptional

Popular amenities

  • Pool
    Pool
  • Parking available
    Parking available
  • Breakfast included
    Breakfast included
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning

Explore the area

Map
Trappe, MD
  • Bill Burton Fishing Pier State Park
    3 min drive
  • Dorchester County Visitors Center
    6 min drive
  • Dorchester General Hospital
    7 min drive
  • Cambridge, MD (CGE-Cambridge - Dorchester)
    12 min drive

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 King Bed

1 bathroom

Private bathroom

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchenette
Garden
Dining Area

About this property

5 bedroom Bed and Breakfast on the Choptank River

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.

Property manager

Michelle Gladmon

Languages

English

Amenities

Pool
Breakfast included
Air conditioning
Parking available

Similar properties

Property grounds
The Anchorage B&B - The Bounty
Pool
Breakfast included
Air conditioning
Outdoor space
10.0 out of 10, (10 reviews)
The Anchorage B&B - The Bounty

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM

Children

Adults only
If supervised at all times

Events

No events allowed
Please speak with Property Owner first

Pets

No pets allowed

Smoking

Smoking is not permitted
Outside only
The barn is off limits. The pool is available, please bring your own beach towels.
Quiet time after 10pm.

Important information

You need to know

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
Note from host: Please speak with Property Owner first
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is required for transport to and from this property

About the area

Trappe

Located in Trappe, this bed & breakfast is on the waterfront. Choptank River Lighthouse and The Third Haven Friends Meeting House are local landmarks, and some of the area's attractions include Ruark Boatworks and Richardson Maritime Museum. Bay Country Shop and Easton Cycle and Sport are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Trappe, MD

What's nearby

  • Dorchester County Visitors Center - 6 min drive
  • Harriet Tubman Museum and Educational Center - 7 min drive
  • Choptank River Lighthouse - 8 min drive
  • Long Wharf Park - 9 min drive
  • Great Marsh Park - 12 min drive

Getting around

  • Cambridge Station - 11 min drive
  • Easton, MD (ESN-Easton - Newnam) - 23 min drive

Restaurants

  • ‪Chick-fil-A - ‬8 min drive
  • ‪Starbucks - ‬8 min drive
  • ‪Great Wall Chinese Restaurant - ‬9 min drive
  • ‪Lil' Bitta Bull BBQ - ‬11 min drive
  • ‪Dairy Queen - ‬7 min drive

Frequently asked questions

Does 5 bedroom Bed and Breakfast on the Choptank River have a pool?

Yes, this property has an outdoor pool.

Is 5 bedroom Bed and Breakfast on the Choptank River pet-friendly?

No, pets are not allowed at this property.

What time is check-in at 5 bedroom Bed and Breakfast on the Choptank River?

Check-in begins at 3:00 PM.

What time is check-out at 5 bedroom Bed and Breakfast on the Choptank River?

Checkout is at 11:00 AM.

Where is 5 bedroom Bed and Breakfast on the Choptank River located?

Situated on the waterfront, 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 Christ Episcopal Church are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 19 out of 21 reviews" "
Rating 8 - Good. 2 out of 21 reviews" "
Rating 6 - Okay. 0 out of 21 reviews" "
Rating 4 - Poor. 0 out of 21 reviews" "
Rating 2 - Terrible. 0 out of 21 reviews" "

10/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

frank s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great view of cambridge
Very relaxing. Easy directions. Restaurants, music and art works…all within distance. Easy ….Peasy!
Stayed 2 nights in Apr 2024

8/10 Good

beth S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Always a great time
Beautiful property, great hosts, lots of fun - great area; second time staying
Stayed 2 nights in Oct 2022

10/10 Excellent

Rich J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a view!!
My wife and I visited the Chesapeake area for a short relaxing weekend. This property was perfect. Woody and Michelle were fantastic hosts. They were very helpful suggesting places to visit. The breakfast was fantastic both days. The accommodations were spotless and comfortable. To top it all off the view of the bay was amazing. Great spot right on the water, we were able to sit and enjoy the peace and quiet of the bay. Will definitely come back to this wonderful spot on our next visit to the area.
Stayed 2 nights in Sep 2022

10/10 Excellent

Sian J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, relaxing get-away. Great food!
Couldn’t have asked for a nicer B&B. Hosts were wonderful - gave us great restaurant and activity recommendations and breakfast was delicious. Perfect weekend!
Stayed 3 nights in Jun 2022

10/10 Excellent

John C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Host,Great Room,Great Time!
The Host were exceptional . Very attentive. Room and Bathroom very large and very clean. Great view sitting along the river watching the sunset. We definitely will stay there again in the future.
Stayed 2 nights in Jun 2022

10/10 Excellent

Marcie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Anniversary get away
This was such a quiet and peaceful place to stay. We needed some downtime alone, and we could not have picked a better place. Woody and Michelle were excellent host, and the breakfast was absolutely delicious. Look forward to another stay there.
Stayed 2 nights in Apr 2022

10/10 Excellent

Joshua V., Lancaster, PA

Liked: Cleanliness, check-in, communication, location, listing accuracy
I would have paid more (a little Gem)
I’d definitely book to stay here many more times. The cleanliness of the room, the privacy of the property and isolated distant away from the highway (no traffic noise), the very well kept and manicured acreage of lawn for a special venue such as wedding, graduation, baby shower as only to complement the priceless view of the Chesapeake Bay, about 100 yards away to the room!!!
Stayed 2 nights in Oct 2021

10/10 Excellent

Kate W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exceptional stay!
Exceeded our expectations! Setting was beautiful, breakfast was delicious, hosts were friendly and accommodating. Everything was great!
Stayed 3 nights in Sep 2021

10/10 Excellent

Denise S., Baltimore, MD

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay
We had a great stay at Michelle and Woody's place. Exactly as pictured and described. Perfect location as a jump off point to many Eastern Shore activities - an easy drive. Their property is beautiful, quiet, serene. Breakfast is a plus and delicious. Michelle and Woody are gracious hosts answering all of our questions and make excellent recommendations for the area. Hope to visit with them again soon.
Stayed 2 nights in Sep 2021

10/10 Excellent

Whitney M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing and Beautiful!
Gorgeous accommodations and excellent food by friendly and helpful hosts!

10/10 Excellent

Joan C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Couldn’t have been better!
The Anchorage is a beautiful property and was the perfect spot for a few days on the Eastern shore. Michelle and Woody were wonderful hosts and helped us make the most of our biking trip. Their knowledge of the area made our outings perfect. We will be back in the fall!
Stayed 2 nights in Jun 2021

10/10 Excellent

LISA A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location for quiet and exploring.
My husband and I thoroughly enjoyed our stay. The Anchorage is just as beautiful as the pictures show. Michelle and Woody were very welcoming. They gave us wonderful suggestions on places to eat and visit during our stay. The breakfasts that Woody prepared each morning was delicious and unique. The 4 days we spent at The Anchorage were relaxing and rejuvinating.
Stayed 4 nights in Jun 2021

10/10 Excellent

marcy s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay at the Anchorage
I reserved this Inn for my husband's birthday, and the hosts and the property did not disappoint. Woody and Michelle were welcoming, gracious, and helpful, taking care of all of our needs, and allowing us to kick back and enjoy this wonderful property. We stayed in the Santa Maria which had lots of light, pretty tile, and plenty of room to relax. We enjoyed the scrumptious and decadent breakfasts in the meticulously decorated dining room, where we had a fantastic view of the Choptank River. We also took advantage of the free kayaks and went out each morning to explore, coast, and unwind. This Inn provides the right balance of in house activities on the property, i.e. volley ball, playing croquet, kayaking, etc and is also near charming towns such as Cambridge, Easton, and St. Michaels. My husband and I had such a wonderful time and will rave about The Anchorage to all of our friends and family members.
Stayed 2 nights in May 2021

10/10 Excellent

Jennifer G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Experience with Amazing Hosts
My husband and I enjoyed a short 2 day stay at this adorable bed & breakfast! Woody & Michelle rolled out the red carpet, meeting us as we pulled up. They gave us a quick orientation, including some history of this 1800’s property and recommendations on local restaurants and places to visit. Our room was bright and clean; well equipped with a king bed, kitchenette, table with seating, and full bath with walk-in shower. The stunning views of the Choptank River and Woody’s unique and scrumptious breakfasts are in competition as my favorite parts of the trip. We ate breakfast in the main house, at a table for two by the large picture window, overlooking the pool and the expansive view of the river. Music played softly in the background as Woody spoiled us with luxuriously displayed and prepared food, elevated by herbs, fresh from Michelle’s garden. I am not big on breakfast, but after the first breakfast, I couldn’t not wait to see what we would be served the next morning! We enjoyed the other amenities as well, including walking on the beach and collecting sea glass, watching the sunset from the beach as well as by the bonfire. Since our trip was so short we didn’t have the opportunity to get to do everything, but definitely plan to return. We’re looking forward to napping in the hammocks, creating our own painting, kayaking from the beach, lounging around the pool and of course...enjoying another amazing breakfast!! You need to stay longer than 2 nights to experience all they have to offer at The Anchorage. Check them out on social media and online at Anchorage1800
Stayed 2 nights in May 2021

10/10 Excellent

John S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay at the Anchorage
Woody and Michelle were great hosts. The property is magnificent and well maintained. The room was very clean and spacious. The hosts are very well aware of how to handle social interactions during these days of Covid. We bought crabs and beer and shared with other guests followed by a fire on the beach. Super relaxing! Ask Michelle about her local honey and sour dough bread :)
Stayed 2 nights in Sep 2020

10/10 Excellent

Kyla O., Westminster, MD

Liked: Cleanliness, check-in, communication, location, listing accuracy
We Loved This B&B!
From the beautiful rooms, bay views and private beach, gourmet breakfasts and wonderful hosts Woody and Michelle, every aspect of our stay was perfection! We will definitely come back and bring friends!
Stayed 2 nights in Sep 2020

8/10 Good

Patrick K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quick getaway
Woody and Michelle were gracious and accommodating. The views from the house and the beach were outstanding. Breakfast was great (ask for the ‘world famous’ banana/blueberry corn muffin!).
Stayed 2 nights in Aug 2020

10/10 Excellent

Katie P., Olney

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect getaway for our anniversary
We were looking for a quiet, private and tranquil place to celebrate our anniversary (especially since Covid) and reconnect. The Anchorage was a perfect getaway ; easy to get to, stylish, clean and serene. The private beach, hammocks and pool were perfect way to recharge. Woody & Michelle were great hosts, very welcoming and charming (& Woody cooks a great breakfast 👍😊). There are a few great restaurants near by and several more a little further away. We look forward to going back sooner than later. We highly recommend!
Stayed 2 nights in Jul 2020

10/10 Excellent

Ginny A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
IMMD
Clean and cozy accommodations. Owners were accommodating, friendly and not overburdening. We came and went as we pleased. Would love to return! Beautiful view of the river!
Stayed 2 nights in Sep 2019

10/10 Excellent

Billie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Can’t wait to come back!
My husband and I agreed we had one of our best weekends ever at Anchorage B & B! From the the warm welcome we received from owners Woody & Michelle, to our last look at the perfectly beautiful setting right on the water as we left, our stay was perfect! Beautiful beach, shore birds & wildlife to enjoy, delicious breakfasts, and the owners had so much information about things in the area to do. It was a perfect weekend, and we look forward to many visits to come & will bring the whole family next time! Thank you so much Woody & Michelle.
Stayed 2 nights in Aug 2019

10/10 Excellent

Elise A.

Perfect Ironman Location!
Woody and Michelle are great hosts in an amazing location! Located just over the bridge looking right across the river at Ironman Village, this is the perfect location for your race weekend. Brand new rooms in a separate guest house with kitchenettes are super spacious. The historic main house and patio area are beautifully restored by Woody himself. Treat yourself to a long weekend here - you won’t regret it!
Stayed 2 nights in Jun 2019

About the host

Hosted by Michelle Gladmon

Host profile image
My husband Woody and I recently moved to the Eastern Shore of Maryland. We both love to travel, cook, are avid cyclists and enjoy nature and the outdoors. We look forward to welcoming visitors to our home and sharing what the Eastern Shore has to offer!

Why they chose this property

Woody and I chose to buy The Anchorage because we both love old houses and wanted to live on the water plus we really love the Eastern Shore of Maryland and all the great things it has to offer. The location is great - 5 minutes from Cambridge, 15 minutes to Easton or Oxford, and St. Michaels is also nearby.

What makes this property unique

Having 500 ft. of beach right on the water is a definite benefit for our guests, and the water views are stunning with tons of bird and boat watching. We have several kayaks for use that can be launched right off the beach to explore the area by water. This is a private setting and very quiet and peaceful. Plus the sunsets are spectacular!

Languages:

English
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