Dames Quarter Rentals USA Maryland Dames Quarter

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD | House in Deal Island Historic District

9.6 (9 Reviews) |   Pet Friendly   3 Bedrooms  1 Bathroom  8 Guests
Dames Quarter House | Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

3 Bedroom House in Dames Quarter, Deal Island Historic District

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.

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD is located in Dames Quarter. Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD provides accommodation, featuring Security/Safety, Fireplace/Heating, Barbecue/Outdoor Cooking, among other amenities. This House features Security/Safety, Fireplace/Heating, Barbecue/Outdoor Cooking, to make your stay a comfortable one.

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD has 3 Bedrooms , 1 Bathroom, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have rated it 2, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Dames Quarter has interesting places to visit. If you want to learn more about the House in Dames Quarter, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
  • Fireplace/Heating
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy Events allowed: family gatherings, birthday parties, weddings;maximum event attendees: 30
Check-in Check-in time starts at 4:00 pm minimum check-in age: 18
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy 1 total (up to 50 lbs per pet) pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy Smoking is not permitted
Other Policy 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 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 parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 30 special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Deal Island Historic District, 21821, USA

What Our Guests say 500 + Reviews

May 23, 2025 04:10:52 AM
Summary: 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!
Terry R. Terry R.
May 12, 2025 10:10:44 PM
Summary: 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.
Cherie B. Cherie B.
Apr 19, 2025 02:13:10 AM
Summary: 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.
Ryan S. Ryan S.
Mar 19, 2025 05:34:06 AM
Summary: Very clean and charming home we will be back again!
Sarafina D. Sarafina D.
Feb 5, 2025 05:06:34 AM
Summary: Great house, attentive host, and a beautiful and quiet setting
Timothy S. Timothy S.
Jan 12, 2025 07:57:55 AM
Summary: The house worked out good for 4 hunters.
Landon S. Landon S.
Dec 1, 2024 09:29:04 PM
Summary: 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.
Robert P. Robert P.
Nov 12, 2024 09:59:06 PM
Summary: 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!
Monika B. Monika B.

FAQ's

Is this Dames Quarter house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Dames Quarter house have a swimming pool?

No, this Dames Quarter house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Dames Quarter house?

Best-rates for the Dames Quarter house starts from $127 per night with includes Laundry, Security/Safety, Fireplace/Heating, Barbecue/Outdoor Cooking, Child Friendly, Internet, Air Conditioner, Pet Friendly, Bedding/Linens, Kitchen StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Dames Quarter house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house 2 stars or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Dames Quarter house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Dames Quarter house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Dames Quarter house?

Based on the information reported by the owner or manager, the Dames Quarter house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Dames Quarter house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Dames Quarter house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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