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

2.0 star property
Deal Island vacation home with kitchen

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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

9.6 out of 10
Exceptional

Entire home

3 bedrooms1 bathroomSleeps 81160 sq ft

Popular amenities

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

Explore the area

View in a map
Deal Island Historic District, MD
  • Place, Crab Island
  • Place, Rock Island
    ‪8 min drive‬
  • Place, University of Maryland Eastern Shore
    ‪33 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪56 min drive‬

Room options

About the neighborhood

Deal Island

In Deal Island .You'll find Shark Fin Shoal and Rock Island within 3 miles (5 km) of this vacation home. Whitehaven Historic District and Mount Vernon Park are also within 20 miles (32 km).
View more Vacation Homes in Deal IslandOpens in a new window

What's nearby

  • Rock Island - 8 min drive - 3.2 miles
  • University of Maryland Eastern Shore - 33 min drive - 19.9 miles
  • Salisbury University - 49 min drive - 32.3 miles
  • Wicomico Youth and Civic Center - 53 min drive - 36.8 miles

Getting around

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

Restaurants

  • ‪Arby's Restaurant and Bar - ‬6 min drive
  • ‪Blue Heron Seafood Co - ‬10 min drive
  • ‪Crab Bytes - ‬4 min drive
  • ‪shedders at Wenona,Md - ‬5 min drive
  • ‪Lucky's - ‬3 min drive

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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  • Washer
  • Dryer
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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

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 are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 50 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

Events allowed: family gatherings, birthday parties, weddings

Smoking

Smoking is not permitted

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 30.

Frequently asked questions

How close is Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD to the airport?

This vacation home is 33.2 mi (43-min drive) away from the Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) airport, the closest popular airport to the property.

Does Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD to the beach?

This vacation home is 19.7 mi (38-min drive) from Mount Vernon Beach.

Does Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD?

No, there is no casino at this vacation home.

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.

Is there free parking at Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD?

Free parking is not available at this vacation home.

Does Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD have a pool?

This vacation home does not have a pool.

Does Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD have a spa?

There are no spa services available at this vacation home.

How close is Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD to downtown Deal Island?

This vacation home is 0.1 mi away from Deal Island.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 8 out of 10 reviews
Rating 8 - Good. 2 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

Reviews

10/10 Excellent

Robert P.

Liked: Cleanliness
Second stay and was very nice. Home is well equipped and will be back again.
Stayed 4 nights in Aug 2025

8/10 Good

Clarky

Liked: Cleanliness
Loved the location and property, very welcoming and quiet. Perfect for a little get away
Stayed 4 nights in Aug 2025

10/10 Excellent

Terry R.

Liked: Cleanliness

Amazing!

This was the best rental! Cute little early 1900s farmhouse with beach decor. The kitchen js well equipped and there js a nice grill outside. The firepit was a nice way to spend evenings as was the screen porch.The little beach about a 5 minute ride/15 min walk was an added bonus! We will definitely rent here again!
Stayed 4 nights in May 2025

10/10 Excellent

Cherie B.

Liked: Cleanliness

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

Ryan S.

Liked: Cleanliness

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

10/10 Excellent

Sarafina D.

Liked: Cleanliness

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

Deal Island Getaway

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

8/10 Good

Landon S.

Liked: Cleanliness

Hunting trip

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

10/10 Excellent

Robert P.

Liked: Cleanliness

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

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