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Homestead

3 Bedrooms
2 Baths
5 Guests
Chincoteague Island
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 included with your reservation.

- 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.

Turtle Bay

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Screened Porch
Pool
Internet

Treat yourself to an unforgettable stay at Turtle Bay! This brand new construction will leave you in awe. The coastal décor is everything perfect for a beautiful vacation. Immerse yourself in the plentiful views, sit and sip your morning coffee or evening beverage from the screened porch or cozy up by the fire in the living room. Cooking will be a breeze in the tastefully laid out kitchen featuring stainless steel appliances and granite countertops. Enjoy the large open floor plan and the inviting owners suite with a queen sized bed and  a walk in shower. The other 3 bedrooms also feature queen sized beds, one with a smart tv as well as two full bathrooms.

Turtle Bay is nestled in the beautiful community of 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).

- No smoking is permitted on the premises.

- Linens and towels are included with your reservation.

- 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.

- 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. 

Island Sunrise

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Internet

Island Sunrise is a gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly, but it offers a deep water boat dock and 3 spacious decks. Aptly named, the sunrises and views of Assateague Island and the Assateague Channel truly are second to none! If you're looking for a nice, relaxing vacation home to enjoy your vacation, look no further. Island Sunrise is it!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $200 per pet will apply. Maximum number of pets allowed: 2. 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.

Lazy Days

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet

Located on Main Street just north of town, "Lazy Days" may be just the perfect spot for your vacation! Cute and comfortable, this cottage is adorned with nothing but island charm. Downstairs features a cozy living room with flat screen TV, an eat-in kitchen with a back door that leads out to the yard, a full bathroom (tub & shower), a bedroom with a Double bed, and a second bedroom with a Twin bed and Bunk bed (2 Twins). Upstairs you'll find another bathroom (shower only) and bedroom with Queen size bed. (Please note: the stairs are steep and the upstairs has "knee walls".) The Chincoteague Bay is just a stone's throw - across the street - from the front steps... enjoy snippet water views! Nature trails, dog park, and downtown Chincoteague are just a minute or two by car. Enjoy a relaxing vacation at this affordable beach house!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 4. 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.

Golden Hour Getaway

3 Bedrooms
2 Baths
8 Guests
Cape Charles
Gas Grill
Internet
Outdoor Shower

Welcome to Golden Hour Getaway!

Porch mornings. Beach afternoons. Long dinners with the people you love.

Slow down, settle in, and experience Cape Charles the way it was meant to be enjoyed.

Tucked along a quiet, tree-lined street beside Central Park, this beautifully restored 1920s home places you in the heart of it all while giving you a peaceful place to retreat at the end of the day. Here, mornings begin with coffee on the front porch, afternoons are spent at the beach, and evenings unfold over long dinners with the people you love.

From the moment you arrive the charm of Cape Charles surrounds you. The home’s classic architecture and welcoming porches capture the spirit of this historic beach town, while thoughtful updates provide all the comforts you want for an effortless getaway.

Step inside and you’ll find a home full of character-from soaring ceilings and original wood floors to intricate moldings and a beautiful grand staircase. At the center of it all is the sunroom, where floor-to-ceiling windows fill the space with sunlight. Curl up with a good book, enjoy a quiet morning, or gather together after a day exploring the Eastern Shore.

The fully stocked Kitchen makes staying in just as enjoyable as going out, with stainless steel appliances and quartz countertops ready for everything from morning pancakes to a family dinner. Gather around the dining table with room for up to 10, pour a drink from the beverage fridge, and linger a little longer. After all, you’re on vacation.

With three comfortable bedrooms, there’s room for families and groups to spread out and make themselves at home. The primary bedroom features a king bed for a restful night’s sleep, while the second bedroom features a queen bed and cozy reading nook. The third bedroom is designed with families in mind, offering a full-size bed plus a bunk configuration with a full bed and twin above.

The backyard makes outdoor time easy, with a gas grill for laid-back dinners, a storage shed stocked with beach gear, and an outdoor shower to rinse off after a day at the beach. There’s even dedicated golf cart parking and charging, making it simple to hop in and explore Cape Charles like a local.

Everything Cape Charles Has to Offer

One of the greatest luxuries of this home is its location.

Leave the cares behind and stroll to the beachfront, wander through the charming downtown streets, browse local boutiques, stop for ice cream, enjoy dinner, or spend an afternoon by the water. With Central Park just outside your door and the beach and downtown just a short walk away, you’re perfectly positioned to experience the best of Cape Charles.

Come for the beach. Stay for the Charm. Slow down for a few days and make yourself at home in one of Virginia’s most beloved coastal towns. 

Property Highlights:

  • Stately, fully restored 1920s Foursquare
  • 3 bedrooms | 2 bathrooms
  • Signature sunroom with floor-to-ceiling windows
  • Chef-inspired kitchen with stainless steel appliances & quartz countertops
  • Dining room with seating for 10 and beverage fridge
  • Multiple outdoor living spaces, including front porch, side porch, and elevated sun porch with park views
  • Backyard with gas grill, beach gear, and golf cart parking/charging
  • Flexible sleeping arrangements ideal for families and groups
  • Fenced yard & off-street parking

Policies:

· No smoking

· No pets

· Linens and towels included

· Advanced reservations subject to rate and availability changes (confirmed in January of arrival year) 

 

Oyster Catcher

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet

Welcome to Oyster Catcher! This home offers a prime location, beautiful views and a deep water dock (6 feet at low tide)!  We encourage you to sit and relax on the large screened porch and enjoy all nature has to offer. Upon entering the home from the side door, you'll be greeted by the the fully equipped kitchen that provides all the essentials for meals at home, while overlooking some of the most beautiful views the Island has to offer. The living room does not lack views either- sit and relax while opening one, or all four, of the large panoramic folding doors that span across the kitchen and living area. Enjoy the sounds of nature or feel the cool salt air breeze. There is a first floor bedroom, with a full size bed and a separate full bath (tub/shower combo) - you have your own access to the screened porch from the first floor room.  The living room also has a queen sleep sofa.  Upstairs you will find two more bedrooms, one with two twins and another with a full. All bedrooms showcase breathtaking views of Deep Creek. Venture outside to the private guest cottage that holds much history from one of the Islands most plentiful seafood shacks. The guest cottage features a queen bed and full bathroom with shower, as well as a floating twin bed. Drop a line or a crab pot at the end of your private dock- maybe you will even get to enjoy a fresh catch for dinner! Oyster Catcher offers a private setting with bountiful plants and greenery, plenty of yard for whole family including your fur babies!  Other amenities include a gas grill and WIFI.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Pet Restriction: 1 med/lg dog OR 2 small dogs under 35 lbs each, NO CATS. 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.

 

Shore Reflections

4 Bedrooms
2 Baths & 1 Half
12 Guests
Cape Charles
Town & Country
Internet

Now available and awaiting your next vacation adventure, this lovingly restored 4-bedroom Victorian home blends traditional charm with modern convenience. Nestled in a picturesque setting with beautiful landscaping and mature trees, you're just a 10-minute drive from the vibrant Cape Charles community. Explore and enjoy downtown Cape Charles, which features a pristine beach, delicious food offerings, eclectic shopping, ice cream treats, coffee shops and so much more!

Spanning 3,000 sq ft, this exquisite property features a layout with high ceilings and wood flooring throughout, enhancing the airy and expansive feel of each room. The main living spaces boast large windows that flood the home with natural light, creating a warm, welcoming atmosphere. Four generously sized bedrooms offer ample personal space for relaxation and rejuvenation. The home also includes 2.5 bathrooms, each maintaining the character of the house with tasteful touches.

Guests will enjoy a beautifully landscaped yard, ideal for leisurely days spent outdoors or entertaining guests in a serene environment. The kitchen, equipped with essential appliances, provides a comfortable space for culinary exploration and seamlessly caters to both casual dining and larger gatherings.

This property is perfect for those who appreciate the beauty of historic homes but expect the functionality needed for a contemporary lifestyle. Make your "home away from home" in a place where tradition meets comfort in the heart of Eastville, VA. Experience the unique charm of this Victorian beauty and the inviting community that surrounds it.

- No smoking is permitted on the premises. 

- Linens and towels are provided for your stay. 

- 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.

Cozy Nest

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water View
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Welcome to "Cozy Nest," a charming home available for your next vacation experience, offering an idyllic retreat with stunning water views! This inviting property spanning over 900 sq. feet can accommodate up to 6 guests, making it an ideal choice for families, friends, or anyone looking to immerse themselves in comfort and tranquility.

 

"Cozy Nest" features two well-appointed bedrooms and two full bathrooms, ensuring privacy and convenience. The primary suite bedroom, encompassing the entire second floor, offers a peaceful haven for relaxation with its serene views, private bath, and private deck access. The first floor provides flexible sleeping arrangements with two twin beds in the bedroom, and a sleeper sofa in the living room. The full bath on the first floor rounds out the convenient layout.

 

The heart of this home is its beautiful outdoor spaces. A screened porch provides a bug-free zone to enjoy the fresh air and scenic surroundings, while the open deck invites you to bask in the sun, stargaze at night, or dine al fresco against the backdrop of picturesque water views. These outdoor areas are perfect for entertaining or simply unwinding after a day's adventures.

 

Pet lovers will be delighted to know that "Cozy Nest" is pet-friendly, and welcomes your furry friends to join in on the family fun. Additionally, with three parking spaces available, guests will find ample parking for their vehicles.

 

Located in a serene setting with captivating water views, this property offers the perfect blend of relaxation and convenience. Whether you're seeking a peaceful getaway or a comfortable base from which to explore the area, "Cozy Nest" promises a memorable stay for all who visit.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 4. 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.

Return

4 Bedrooms
3 Baths & 1 Half
11 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Beautiful waterfront contemporary perched on the edge of Assateague Channel. Enjoy breathtaking vistas of Assateague Island, the lighthouse, the wild ponies and the abundant wildlife. This spacious home boasts a complete line of amenities including a 600' pier/dock with deep water access, and waterside decks and screened porch. This home is great for boaters! The bright and airy open floor plan is highlighted with fine custom windows throughout that frame the beautiful, panoramic water views. In addition, there are 2 private master bedroom suites, both with private full baths, on the main living level. The second level features another two bedrooms and full bath plus a private sleeping area, so there is plenty of room for everyone! Wireless internet available.

- 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.

Misty's Thicket

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Charcoal Grill
Screened Porch
Internet

Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends. Upstairs, you find a great master bedroom with en-suite, a full bathroom off the hallway, and a second bedroom that features a bunk bed and a queen size bed that looks out onto the second-level screened in porch affording amazing Chincoteague Island views.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pets are not 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.

Sunset Bay Villa 221

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Pool
Internet

Buckle up, folks, because Sunset Bay Villa 221 is here to light up your vacation! This fresh-faced beauty just hit the market and is ready to become your new home away from home. Prepare to be blown away by water views so gorgeous, you'll want to frame them! Every nook and cranny of this place has a view that will leave you breathless.

The open floor plan allows you to cook and entertain at the same time. And let's not forget the deck, the perfect spot to kick back and enjoy your morning cup of coffee or unwind with a glass of wine as the sun sets over the water. The primary bedroom is fit for royalty with a king-size bed to cocoon you in comfort. But wait, there's more! Two additional rooms, one with a king, one with two twin beds, so everyone can sleep tight and dream big. There are tv's in each bedroom as well. Don't miss out on this gem! The Sunset Bay Villa Community has an outdoor pool, indoor workout room, and outdoor dining area!

- 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.

New Quarter Townhouse

3 Bedrooms
3 Baths
6 Guests
Cape Charles
Town & Country
Gas Grill
Pool
Internet

Coastal Charm in Cape Charles

Slow down, settle in, and experience the laidback charm of Cape Charles from the comfort of this spacious three-bedroom, three bath condo in New Quarter.

Designed for easy coastal living, this inviting retreat gives you room to spread out while keeping you close to everything that makes Cape Charles special. The condo offers a first-floor primary suite with a queen bed, upstairs you will find two comfortable bedrooms each featuring queen beds and three full bathrooms giving families and groups plenty of space and privacy to relax after a day of adventures. The open living spaces create a welcoming place to gather, while the kitchen makes it easy to enjoy a quiet breakfast before heading out or wind down with dinner at home.

When you’re ready to explore, Cape Charles is just the beginning. Spend the day on the Chesapeake Bay, wander the charming streets of historic downtown, browse local shops and galleries, enjoy a sunset dinner, or simply find your favorite spot to read your favorite author.

New Quarter Townhouse offers a peaceful home base for experiencing Cape Charles at your own pace-comfortable, convenient, and wonderfully coastal.

Good to Know

  • 1st Floor Primary Suite
  • 3 bedrooms
  • 3 full bathrooms
  • Located in Bay Creek
  • Guest will not have access to Bay Creek Amenities
  • Convenient to Cape Charles beaches, downtown, dining, shopping, and local attractions

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.   

- Bay Creek Community amenities are not available with this rental home. 

- 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.

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