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Endless Summer

4 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come enjoy your stay at one of the most sought out locations on the Island. Easy, convenient access to the beach. With the large open floor plan, high ceilings, and easy one level living, you have everything you need at Endless Summer. Bring along your furry friends to make your vacation complete! This home has plenty of room for the whole family to gather. Enjoy the nice screened in porch or the large open front porch with your morning coffee and listen to the serene sounds of nature. The Piney Island Community offers convenient access to a kayak launch located on Pine Drive, just minutes from the home.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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. BREED RESTRICTIONS APPLY. 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.

Egret's Cove

3 Bedrooms
3 Baths
11 Guests
Chincoteague Island
Waterfront
Pet Friendly
Gas Grill
Screened Porch
Hot Tub
Internet
Outdoor Shower

Breathtaking views call your attention at this gorgeous waterfront home! 'Egret's Cove' is located next door to our ever popular sister vacation home, 'Heron's Cove'. Egret's Cove is rich with amenities, leaving nothing to be desired for an enjoyable vacation stay. With the amazing views, blissful sunrises, bay breezes, pet-friendly, you'll be in awe that this bay front home has to offer! This home was built directly on Little Oyster Bay in 2004, and has a large screened porch with a hot tub. Boasting beautiful water views from almost every room, the interior features tasteful decor, lots of natural light and a vaulted ceiling in the living room that lends to the "openness." One bedroom with a king is located on the first floor (with a Jack and Jill bath). The kitchen also features everything you will need to cook for the family while vacationing, and there is a wet bar adjacent to the dining area. In the large open living room you will also find a full size sleeper sofa. Moving upstairs, you'll again be "wowed" by the views! In the loft, you will find a queen sleeper sofa as well as a game table, twin sleep sofa and plenty of room to relax. One bedroom features a king size bed, with a private balcony. Across the hall you will find another bedroom with a queen size bed, lots of natural light and a dedicated workspace. There is a large deck that has a spiral staircase to make your way down to the screened porch.. You will also find two full bathrooms in this space. Each bedroom also features a smart TV for your enjoyment! Outside, experience a private oasis and enjoy a relaxing soak in the hot tub overlooking the Bay while finding peace in the natural elements surrounding the space. Relax on the front deck or by the fire pit - all of which is enclosed by a fence so your furry friends can roam without worries. There is also a shared dock with the home next door, perfect for kayaking or crabbing.

- 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. BREED RESTRICTIONS APPLY. 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.

Sunrise View

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

**Island Living at Its Finest — Where Sunrises Steal the Show**

Welcome to the most breathtaking views Chincoteague Island has to offer. Nestled in the sought-after Oyster Bay I Community, this stunning three-bedroom, three-bathroom WATERFRONT rental home is a haven for those who crave inspiration from the natural world. If you're an artist, writer, creator, or simply someone who finds peace in golden-hour magic, this is where you belong.

Step inside to discover a thoughtfully designed living space that includes a comfortable living room and an additional den — perfect for curling up with a good book or sketching the marshland views that stretch endlessly beyond your windows. View the water from almost anywhere…Feeling playful? Challenge your guests to a round of bumper pool, because every retreat deserves a touch of friendly competition.

The real magic unfolds across multiple levels, where every room has a view!  Climb the spiral staircase to the third-level tower room, where panoramic vistas will leave you utterly speechless. Gorgeous sunsets paint the sky in hues you didn't know existed, and you'll find yourself reaching for a camera — or a canvas — day after day.

Outdoor living shines here with spacious decks ideal for entertaining and a screened porch complete with a ceiling fan, offering bug-free relaxation while the island breeze does the rest. Quietly listen to music and watch the Purple Martins swirl about … just off the porch. It's the kind of space where conversations linger and worries disappear. It's magical.

Boaters delight in the fact that they can tie-up their boat right at the home. Using the community boat ramp makes this easy. Boat, kayak or fish right from the property.

Beyond the home, adventure awaits. Explore the nearby Island Nature Trails for serene walks through coastal landscapes, catch waves at Assateague Beach where wild ponies roam, or bring the family to Maui Jack's Waterpark for splashing fun on warmer days.

This is more than a rental — it's an experience that feeds the soul. Reach out today to secure your ISLAND ESCAPE and experience these legendary sunrises over the bay.

- 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.

Piney Island Paradise

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Internet

Welcome to Piney Island Paradise! This well-furnished townhouse is nestled in a secluded cul-de-sac along East Side Drive and offers some of the best views of Assateague Island and the historic lighthouse located across the channel. The channel on Eastside offers some of the calmest water for kayaking, plentiful crabbing, and great fishing. Enjoy the most beautiful sunrise views from this vacation home along with quiet solitude! This home also offers 2 kayaks for your enjoyment! 

Upon entering this home, you will find a half bath, first floor bedroom with a queen-sized bed, a well-stocked kitchen, living room, and large waterfront deck with plenty of seating to relax, enjoy the wildlife, and watch the ponies grazing on Assateague Island. On the 2nd floor you will find two more bedrooms as well as the laundry area. The main suite features a king-sized bed with a full bathroom and waterfront deck to enjoy the peaceful sounds of nature and beautiful sunrise views. You will also find a 3rd bedroom that easily accommodates 5 more guests. This room features a twin over twin bunk, a twin over full bunk, and a full bathroom with walk in shower. This home also includes a nice assortment of beach chairs and a small attached garage where you can store your bicycles and kayaks. If you are looking for a home with all the amenities and want to enjoy the beauty of Chincoteague & Assateague Island, this is it!

- 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.

Waterman's Daughter

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Water View
Pet Friendly
Charcoal Grill
Internet

We are excited to introduce Waterman's Daughter! This stately townhome is located on a quiet lane off of East Side Drive. The first floor of the home features two bedrooms, both featuring full attached baths! A full size washer and dryer are conveniently located off the hall in between these bedrooms. As you make your way to the second floor of the home, you are greeted by a bright living space featuring a flat screen TV, fireplace, large windows, and doors that lead you out to the second floor balcony that features a table for two with a view. Right beyond the dining area of the home, you will find the fully equipped kitchen that features additional seating for three at the kitchen bar, a stove top oven, microwave, and dishwasher. The large Master bedroom is on the second floor of the home and features yet another full attached bath and wall-mounted flat screen TV. There's even a shared waterfront area - perfect for launching your kayak or canoe. This home is truly the perfect setting for your next Chincoteague Island vacation; clean, relaxing, and accommodating! Call us or book online today!

- 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 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.

Sunrise/Sunset

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Town & Country
Gas Grill
Internet

Looking for an island home that won't drain your savings? This two-bedroom, two-and-a-half-bathroom townhouse delivers comfortable Chincoteague Island vacationing with a price tag that actually leaves room for ice cream cones and beach days.

The heart of this home is its standout four-season room, a bright and breezy spot built for year-round enjoyment. Curl up with a book in the dead of winter or throw the windows open when the salt air calls — either way, you'll find yourself drawn back to this cozy corner again and again. An electric fireplace adds a flicker of warmth to chilly evenings, perfect for unwinding after a day of island wandering.

Both bedrooms sit upstairs, tucked away from the main living areas for a little extra peace and quiet when it's time to rest. Step outside and you'll discover a fenced yard, ideal for letting pets roam, hosting a casual cookout, or simply claiming your favorite lawn chair under the open sky.

Location? You've hit the jackpot. Veteran's Memorial Park is practically next door, complete with a playground, courts, and plenty of green space. The annual Carnival is just around the corner for summertime fun, while Island Foods handles grocery runs in a flash. When adventure calls, Maui Jack's Waterpark and the legendary Assateague Beach — wild ponies included — are a short hop away.

Affordable, comfortable, and perfectly positioned. What are you waiting for?

- 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 pets allowed: 3. Pet Restriction: 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.

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) 

 

Sunset Bay Villa 206

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Charcoal Grill
Pool
Internet

Villa 206 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with private luxury bath and private exit to the waterside balcony. Villa 206 will sleep 8, and there are a total of 4 TVs. A laundry room within the unit houses your washer & dryer. Your stay also includes use of the Sunset Bay marina, pool and fitness areas. Come. Enjoy! Note: This property does not have a boat slip, however, use of the marina is included. 7-night minimum stay is required during all seasons.

- SPECIAL NOTE: This rental home has a 7 night minimum year 'round. 

- 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.

Poole's Cove

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Gas Grill
Screened Porch
Internet
Outdoor Shower

Nestled just off Main Street with the water as your backdrop, Poole's Cove is a lovingly curated escape that feels inspired and inviting. Every detail of this thoughtfully decorated home invites you to slow down, breathe deeply, and truly settle in.

The layout is designed for both togetherness and solitude. The primary bedroom suite anchors the main house, while a breezeway connects you to a separate wing with two additional bedrooms and bathrooms — perfect for families or couples who want space to gather and space to retreat.

Step into a large screened-in deck and up to the rooftop deck, where water views, golden sunsets, open skies, and unforgettable stargazing await. When you're ready to unwind indoors, the upstairs office and library is a wonderful place to lose yourself in a good book.

And the best part? Poole's Cove has just undergone a complete top-to-bottom renovation. Brand new kitchen, floors, bedrooms, bathrooms, and furnishings throughout — plus significant exterior updates. The Poole's Cove you've always loved is now better than ever.

This isn't just a place to stay. It's an experience.

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Please note: Due to this home's unique floor plan and open deck railings, it may not be suitable for young children. This is a non-smoking, pet-free property. Linens and towels are 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.

Lighthouse Estates #8

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Water View
Pet Friendly
Boat Dock
Charcoal Grill
Pool
Internet

Welcome to Lighthouse Estates #8, formerly known as 'Natalie's Nook'! This 2 bedroom beach retreat is located in the popular Lighthouse Estates community on the East Side of Chincoteague Island. Enjoy all the amenities and features one could desire during their vacation - a pool, water & lighthouse views, a pier perfect for fishing, crabbing or kayaking, not to mention a vacation rental filled with all the comforts of home! Downstairs you'll find an open floor plan with living room, kitchen, dining area and powder room. Upstairs features 2 bedrooms (one master ensuite with private bathroom and water view balcony) and a full bathroom off the hallway. Lighthouse Estates #8 is conveniently located to The Pearl Restaurant, the waterfront Memorial Park, boat rentals, the Town public boat ramp & more! Come for a fabulous, relaxing stay! . 

- 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: 1. Pet Restriction: 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.

Assateague Overlook

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water View
Charcoal Grill
Internet

This property has a location that is rich with views and amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run and play, or fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen sleeper sofa). You'll also find a full bath on this level. The second floor offers a queen bedroom with a private deck that has unlimited views of the Assateague Channel. The second bedroom (upstairs) has two twin beds and you'll find another full bathroom on the second level as well. Need more space? Rent Channel Lookout next door! (Waterfront area, dock, pier and playground equipment pictured are community property at Memorial Park.)

- 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.

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.

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