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Mermaid Crossing

3 Bedrooms
2 Baths
10 Guests
In Town
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Internet
Outdoor Shower

Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2 full baths, well-equipped kitchen, dishwasher, washer/dryer, outdoor shower, 1-car garage, Direct TV, wireless internet, DVD, BBQ grill, 4 adult beach cruisers (bring your own helmet), 2 kayaks, crab traps and net, games, books, puzzles, and some beach gear!

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Homestead

3 Bedrooms
2 Baths
5 Guests
North Main
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Set back across the street from Chincoteague Bay, Homestead sits on 30 acres of basically pristine land. A cozy cottage, originally built in 1890, had been updated but the owners kept the original charm of yesterday but with the comfort of today. Now that charm and comfort has been expanded. A new addition offers a great room with a modern kitchen, dining area and room to stretch out and relax. The design includes oversized windows, sliding doors and a sky light. The house now has 2 screen porches and a balcony that lets you feel as though you are living in in a nature preserve! Homestead sleeps 5 but best suited for 4 adults. There are now 2 full sized bathrooms. Amenities include bikes, beach chairs and umbrellas: games, crayons and colored paper and good parking. And as part of the property, you?ll vacation alongside the oldest home on the island, The Captain Timothy Hill House, listed on the National Register of Historic Places. With a tidal pond in front and unspoiled woods in back, Homestead is private, quiet and with lots of room outside. A perfect retreat! So relax on one of the porches, feel the breeze from the bay, watch the animals and birds that come by or take an outside shower under the stars. The Homestead that so many have come to love is still the same?just more to love!

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- No pets permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Dockside

3 Bedrooms
3 Baths & 1 Half
8 Guests
East Side
Waterfront
Boat Dock
Gas Grill
Internet

Located on the Assateague Channel, this is your chance to watch the ponies from your own deck. A wonderful panoramic view awaits you?to the left is the Assateague Bridge; to right of the bridge is the Assateague Lighthouse and ponies; and to the far right is Tom?s Cove and the ocean inlet. Come and fish from your own dock and tie your boat along side! Inside you will find central heat/air, 3 decks, all appliances, gas grill, satellite TV & DVD player and internet access. Enjoy evenings resting beside the wood fireplace (off-season).

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Porter's Barn

1 Bedroom
1 Bath
2 Guests
Mainland
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

Porter's Barn, where luxury meets seclusion on the water's edge...

There is a fanciful quality to this secluded property where nature's beauty and luxurious accommodations coexist in quiet harmony. Located on the banks of Holden's Creek, a headwater of the Chesapeake Bay and a 20-minute drive to the pristine white sand Atlantic beach on Assateague Island, Creek House Guest Cottages are private, convenient, and offer bespoke modern amenities. Explore life off the beaten path and take a true vacation. Whether you are kayaking or paddle boarding on the creek, sitting by the fire pit, biking down country roads or going to the beach, you will find plenty to do or enjoy doing nothing at all. The views of the creek are magical at any time of the day or night from inside your cottage or from any vantage point on the 3-acre property. The Cottages have been designed and decorated by a professional interior designer.

'Porter's Barn' has partnered with our friends at Sun Outdoors Resort (located less than 2 miles from the house) so that all guests may enjoy the fun resort amenities FREE OF CHARGE. This extra bonus includes a private beach w/ water rentals, pool, playground, "snak shak", comfort stations & more! 

Shared amenities include: a gas grill, 20 ft. radius fire pit, 2 kayaks, a SUP, and 2 bicycles. There is a boat launch on the property and two docks (one floating). Linens and towels are provided.

Porter's Barn: 900 square ft. Full Kitchen and Laundry Room. Marble Bathroom. Sleeps 2 (Queen Bed). Outdoor Shower. Smart TV. WIFI

In addition to Porter's Barn, the compound is also home to two other luxurious dwellings: Hosta Cottage and Creek House. All combined, The Creek Compound will accommodate 18 with no parking problems. Please note that this listing is for Porter's Barn only; the other two homes - Creek House and Hosta Cottage - must be booked separately. A direct inquiry should be sent for special event pricing or if you wish to rent the entire compound.

- Linens and towels are included with your reservation. 

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival. Limitations: one dog only. No pets on the furniture, please.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Herbie's Hideaway

3 Bedrooms
3 Baths
8 Guests
South Ridge
Water Access
Gas Grill
Screened Porch
Internet

Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beautiful views of Assateague Island. The oversized chef's kitchen offers ample room for family gatherings and preparing meals, and it compliments the spacious dining area that opens up to the large screened porch. Beautiful custom windows and large sliding doors complete the open and airy floor plan. The geothermal heating/ac system lends to your ultimate vacationing comfort! Close to Memorial Park (playground, basketball, tennis, trails, water access) and directly across the street from a family restaurant! For larger groups or family reunions, check out nearby Moon Rising or Wildflower!

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Diving Duck

5 Bedrooms
2 Baths & 1 Half
10 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Hot Tub
Internet
Outdoor Shower

If you're looking for the complete vacation package, look no further! This 5 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room with access to the waterside deck, a large dining area, kitchen with all the counter space you'd ever need, a half bathroom, and the master bedroom with private bath (with custom tile shower and soaking tub). Upstairs features a landing area with sofa and foosball table, 4 more bedrooms and another full bathroom. Aptly named, 'Diving Duck' is the perfect spot for watching the ducks and wildlife pitch in the bay just out the back door. There's even a floating dock perfect for launching canoes and kayaks! And as if all of that is not enough, the Captains Cove community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. (Fee applies for usage of community amenities.) This rental home is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions). What more could you ask for? Book your stay at 'Diving Duck' today! Additional game room with wet bar and pool table, and a private hot tub. All of this in addition to interior updates and renovations!

- No smoking is permitted on the premises. 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival.  

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

- Community amenities require passes for an additional fee. Although the rental home can accommodate up to 10 guests, only 8 guests are permitted to use the community amenities (pool, etc.) at a time.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities. No Sunday check-ins or check-outs are permitted. 

 

Sea Charm

3 Bedrooms
2 Baths
8 Guests
In Town
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Charming in-town 3 bedroom home with a day-bed alcove, 2 baths, large fenced yard, carport and screened porch. Located on a quiet street, but a short walk to downtown shopping, movies and restaurants. Expanded Master Bedroom with claw foot tub and king size bed. Amenities also include outside (hot/cold water) shower and 2 TVs. 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

The Great Escape

5 Bedrooms
3 Baths
11 Guests
Cape Charles
Screened Porch
Internet

Discover the charm of Cape Charles in this beautifully restored 5-bedroom, 3-bathroom house, available for your next vacation adventure. Nestled in the heart of downtown, "The Great Escape" places you just minutes away from a vibrant selection of shopping, dining, and entertainment options, including local ice cream shops and mini-golf. Whether you're enjoying the bustling town scene or relaxing at home, this property offers both convenience and comfort.

Step onto the inviting open front porch where you can sip your morning coffee while soaking in the town views. Alternatively, the screened porch provides a tranquil retreat to unwind in the evenings without the pesky insects. Inside, you’ll find a clean and comfortable interior with ample living space that caters to both large and small families alike.

"The Great Escape" is ideal for those seeking a blend of small-town charm and modern amenities, all within walking distance of Cape Charles' delightful attractions. Whether you're settling down with your family or looking for a scenic change of pace, this vacation home promises a lifestyle of ease and excitement. Don’t miss out on making this house your new home away from home — book your getaway today!

- Linens and towels are included with your reservation. 

- No smoking is permitted on the premises. 

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

 

Lighthouse View

3 Bedrooms
2 Baths
8 Guests
East Side
Water Access
Pool
Internet

Lighthouse View is located on the east side of our island and includes a private community pool for your enjoyment. The 3 bedroom, 2 bath townhouse features two first floor bedrooms (one with Roku) with full bath in the hallway and a master bedroom suite upstairs. There's water access across the street with a beautiful waterfront lot and dock. Lighthouse View features wireless internet and cable tv (with a premium tier that includes sports, educational, food and other channels).

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival. Pet restriction: limited to one small dog only.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Charlie's Bayside Retreat

3 Bedrooms
2 Baths & 1 Half
8 Guests
South Main
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

This is it! Are you looking for your perfect vacation getaway spot? Look no further. 'Charlie's Bayside Retreat' is everything you'll need for your home away from home, at the beach! The first main level features an open floor plan with a living room that opens up to a wonderful screened porch with comfortable outdoor dining furniture. The open living area also features a large Smart TV with cable and an electric fireplace. A modern kitchen that is fully stocked with everything you could possibly need, also has new appliances and a Keurig coffee maker, breakfast bar, open dining area, and powder room complete the first-floor living space. On the second floor, you'll find two bedrooms, one with a Queen bed and Smart TV and the other with 2 Twins & a Full - both with balconies and a shared full bathroom with dual sinks. The entire third floor is a spacious, private primary oasis with a Queen bed, and a luxurious en suite featuring a deep jetted tub and dual sinks. This bedroom is also equipped with a Smart TV and a balcony with amazing views & Adirondack chairs making it perfect for relaxing or sunbathing. Additional features of this fabulous vacation home include your own private boat slip (#7), pier for fishing and crabbing, fish cleaning station, covered parking area, grill, picnic table, and tons of extras! There's an outdoor shower, and beach gear including beach chairs, beach toys, and an umbrella. Not to mention you're conveniently located on South Main Street - walk to the downtown area (including Ropewalk for food and drinks) or to the annual Fireman's Carnival. The possibilities are endless. Some of the most gorgeous sunsets ever witnessed are from this spot on South Main Street & it is the perfect spot to watch rocket launches from Wallops. It doesn't get much better than this!

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Hailey's Round House

2 Bedrooms
2 Baths
9 Guests
Piney Island
Water Access
Screened Porch
Internet

Check out Chincoteague’s newest Piney Island vacation rental! Hailey’s Round House is in a prime location on Chincoteague, in a quiet development road but just a short walk to the bridge to Assateague and the Maddox Boulevard shops and restaurants!  You could take a bicycle or short drive to the Assateague beach and access to all of the bicycle trails around Chincoteague and Assateague to enjoy the wild ponies or many of the restaurants on Chincoteague.   

Hailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed.  You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay! 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

The Hideaway

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Town & Country
Pet Friendly
Pool
Internet

Welcome to The Hideaway! This charming home offers an inviting blend of comfort, style, and community amenities. This house boasts 1,909 square feet of well-appointed living space designed to accommodate a variety of lifestyles and preferences.

Step inside to discover three spacious bedrooms that promise restful nights and tranquil mornings. The two bathrooms are thoughtfully designed to streamline your daily routines, ensuring convenience for all residents. Embrace the ease of first-floor living, which offers accessibility and a seamless flow throughout the home.

Staying at "The Hideaway" means more than just enjoying the privacy of your own vacation house; it's about being part of a vibrant community. Take advantage of the community pool, where you can cool off on hot summer days or lounge poolside with a good book. Golf enthusiasts will be thrilled with the nearby golf course, providing an excellent opportunity for leisure and networking within steps from your door.

This property is pet-friendly, understanding that pets are cherished members of many families. With four parking spaces, there's ample room for vehicles, ensuring convenience for guests.

Located in a wonderful community known for its friendly atmosphere and scenic surroundings, The Hideaway offers an idyllic setting for those seeking a balanced lifestyle. Whether you're looking to connect with neighbors or enjoy quiet moments at home, this property provides the perfect backdrop for creating lasting memories.

Embrace the opportunity to make The Hideaway your new home away from home and enjoy all the benefits this exceptional property has to offer!

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival. Pet restriction: 2 pet max.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

- Community amenities require passes for an additional fee.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities. No Sunday check-ins or check-outs are permitted. 

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