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Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property

Photo gallery for Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

Dining
Exterior
Beach
Fridge, microwave, oven, stovetop
Exterior

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms1 bathroomSleeps 81160 sq ft

Popular amenities

  • Washer
  • Dryer
  • Kitchen
  • Pet-friendly
  • Barbecue grill
  • Air conditioning

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

Welcome aboard the Rusty Anchor, a beautifully restored 1900s farmhouse that perfectly balances old-school charm with modern-day comfort. Nestled in the heart of Deal Island—a waterman’s haven—this cozy retreat is ideal for families, friends, and anyone craving outdoor adventures and peaceful escapes.
3 Cozy Bedrooms + Charm to Spare
With two private bedrooms upstairs (sleeps 6) and a snug first-floor room (sleeps 2), this farmhouse is ready to host your crew. Fully stocked with a modern kitchen, a comfy living room, and a porch perfect for al fresco dinners, it’s everything you need to unwind and make memories.
Adventure Awaits – Just Minutes from the Chesapeake Bay Deal Island is known for some of the best fishing (Redfish, Striped Bass, Flounder, and Cobia) and waterfowl hunting Maryland has to offer. And if crabbing or kayaking is more your style, you’ll love the cozy beach and boat ramps just a quick 5-minute bike ride away. Not directly on the water? No problem—getting to the shoreline is half the fun.
Want the full waterman experience? Book a local fishing charter or go on a crabbing expedition. Afterward, rinse off in the outdoor shower and relax on the screened porch, watching the stars over the tranquil night sky.
Elevate Your Stay with Special Add-Ons!
Once you book with us, you’ll receive a message with a link to our online store—where you can reserve exclusive add-ons, from kayak rentals to gourmet meal kits. It’s your vacation, exactly how you want it!
Family-Friendly Fun + Outdoor Bliss
Whether it’s biking, beachcombing, or fishing, there’s space for all your gear (and your crew!). With air conditioning, internet, and plenty of outdoor space for games, the Rusty Anchor keeps everyone happy and comfortable.
Easy access? You got it. Our digital keypad entry means no stress at check-in—your custom code will be waiting when you arrive.
Local Treasures + Day Trips Galore
Stock up and dine out in the charming nearby town of Princess Anne, MD, where you’ll find:
Groceries: Food Lion
Dining & Drinks: Beach to Bay Seafood, Caesar’s Pizza Palace, Somerset County Liquors, The Washington Inn & Tavern
Shopping: Hayman Antiques, O Grace and Glory Boutique, Somerset Hidden Treasures
Looking for an extra adventure? Take a scenic drive to Chincoteague Island, VA. Or, if you’re craving a laid-back vibe, stop by Goose Creek Pit & Pub for a Tiki-inspired experience.
Relax. Explore. Recharge.
The Rusty Anchor offers everything you need for a vacation full of fun and relaxation. Whether you’re reeling in fish or kicking back with a good book, this farmhouse getaway makes every moment special.
We’re thrilled to have you as our guest. Book now and get ready to unplug, unwind, and create unforgettable memories on Deal Island.
If anything is needed at all, Please feel free to contact the host Christina Weigand.
Don't forget to stop in Princess Anne for all your grocery, firewood, seafood and produce stand needs.

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Property amenities

Internet

  • Available in the house: WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Outdoor areas

  • Barbecue grill
  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the bay

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Unit size: 1,160 square feet

Similar properties

Property grounds

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, 5 reviews
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 18

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 50 lbs per pet)

Children and extra beds

Children are welcome

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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 30
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Map
Deal Island Historic District, MD

What's nearby

  • Rock Island - 8 min drive - 5.1 km
  • University of Maryland Eastern Shore - 33 min drive - 32.0 km
  • Salisbury University - 49 min drive - 52.0 km
  • Wicomico Youth and Civic Center - 53 min drive - 59.2 km

Getting around

  • Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) - 43 min drive

Restaurants

  • ‪Shredders Restaurant & Bar - ‬6 min drive
  • ‪Lucky's - ‬3 min drive
  • ‪Lucky's Last Chance - ‬3 min drive
  • ‪Arbys Dock Side Bar And Grill - ‬5 min drive
  • ‪Carbin Seafood - ‬19 min walk

Frequently asked questions

Is Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 50 lbs per pet.

What time is check-in at Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD?

Check-in begins at 4:00 PM.

What time is check-out at Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD?

Check-out is at 10:00 AM.

Where is Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD located?

Situated in Deal Island, this vacation home is 2 mi (3.2 km) from Shark Fin Shoal and 2.8 mi (4.5 km) from Rock Island. Whitehaven Historic District and Mount Vernon Park are also within 20 mi (32 km).

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Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 7 out of 8 reviews
Rating 8 - Good. 1 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Sarafina D.

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

We had a great time!

Very clean and charming home we will be back again!
Stayed 3 nights in Mar 2025

10/10 Excellent

Timothy S.

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

Deal Island Getaway

Great house, attentive host, and a beautiful and quiet setting
Stayed 3 nights in Jan 2025

10/10 Excellent

Ryan S.

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

Lovely spring break spot

We wanted a low key place to use as a base for exploring the Eastern Shore, and this was a great spot! An hour or so from almost everything you might want to do, and Deal Island is a relaxing place in its own right, with a little beach and pleasant views of the bay.
Stayed 4 nights in Apr 2025

8/10 Good

Landon S.

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

Hunting trip

The house worked out good for 4 hunters.
Stayed 3 nights in Jan 2025

10/10 Excellent

Cherie B.

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

Heavenly abode

The house is located on Deal Island. It’s a perfect location for peace and quiet and beautiful surroundings. The house is decorated in such a lovely way - beautiful touches throughout. Ample area to walk my dog. Wonderful mornings spent on the screened in porch.
Stayed 3 nights in May 2025

10/10 Excellent

Robert P.

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

Thanksgiving weekend

Our stay was perfect. The home was quite lovely and equipped with all amenities. The location was very nice. The bay was only a 2 minute walk at the end of the street. Highly recommend.
Stayed 3 nights in Nov 2024

10/10 Excellent

Monika B.

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

Memories for a lifetime!!

I booked The Rusty Anchor for my sisters surprise bachelorette weekend getaway… From the first moment, to the last, it was simply amazing. None of us wanted to leave!! Christine was a blessing! Responded to all messages almost immediately. That is pretty rare these days, and was sincerely appreciated. The house was extremely cozy, and there was plenty of room for all of us. Yes, there is only 1 bathroom, but it is quite large, and plenty of room! Do not let that deter you! The house was very clean, organized, stocked, and so comfortable. Loved the kitchen, beds were very comfortable, cute front porch, outside shower, grill, fire pit…you name it, they had it. Extremely quiet and remote area. When standing at the end of the driveway, you can see the water right down the street. Just absolutely stunning. We only had one hiccup… Unfortunately, the day before arrival, a burn ban was put into place for the area given the lack of rain. Within a matter of a couple hours, Christine called, and they came up with another option for us, that worked perfectly. Could not have asked for more! Thank you so very much for an unforgettable experience!
Stayed 3 nights in Oct 2024