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Utter East

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Gas Grill
Screened Porch
Internet
Outdoor Shower

We're pleased to offer you 'Utter East'! Tucked off of a quiet side street in the middle of the island, this home features everything you'd need for a wonderful, relaxing vacation. If you love outdoor space, you'll love the huge screened porch, expansive decks, and beautifully landscaped fire pit sitting area on the pond. Inside the home, downstairs you'll find the living room, an additional den/family room, eat-in kitchen, dining room, two bedrooms and a full bathroom. Upstairs features two more bedrooms and another full bathroom. Don't delay; this home will book quickly! "Where sky and water meet, Where the waves grow sweet, Doubt not, Reepicheep, To find all you seek, There is the UTTER EAST." - From "The Chronicles of Narnia" by C.S. Lewis

- Linens and towels are included with your reservation.

- No smoking/vaping is permitted on the premises, including porches and outdoor areas.

- 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.

Pony View

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

Enjoy your cup of coffee as the sun peeks over the salt marshes of Assateague Island. You can often see a herd of our famous wild ponies grazing to the right of the lighthouse from your private waterfront deck and second-floor balcony - not to mention the copious amounts of waterfowl and other wildlife in the channel. Pony View boasts three bedrooms - A master with queen bed, full bath, and balcony on second floor, as well as another bedroom with a queen on the second floor - along with another full size bath. On the third floor you will find an amazing view of the marsh with the panoramic window and four twin beds, and a beautiful bathroom with a rustic wooden sliding door. The ground floor is where you'll find the hub of the house - fully equipped kitchen with refrigerator, electric range, dishwasher, and plenty of counter space. A dining table and bar seating area, a half bath, and a cozy living area with floor-to-ceiling knockout views. Or enjoy the waterfront deck just outside the living room. Pony View is pet-friendly so your furry friend can enjoy the water view as well. Dock access along with a boat slip is available for your use. Crab and fish right from the house! A deep water boat ramp is found just at the end of the complex for you to drop in. Central air/heat will keep you comfortable year round. There is also a washer/dryer, and an outside grill for your use while you're with us. Memorial Park is just a short walk up the street for a wonderful waterfront park and playground, tennis and volleyball courts, fishing pier, picnic areas, and walking trail.

Please note: Parking is limited to 2 spaces (this includes a boat/trailer if you are bringing one). Max. boat size for docking is 20'. If alternate parking accommodations are needed, please ask. 

- 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. Pet fee is $150 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.

Bayside

3 Bedrooms
2 Baths
8 Guests
Cape Charles
Town & Country
Pet Friendly
Gas Grill
Internet

Welcome to Bayside, your next relaxation haven! This charming 3-bedroom, 2-bathroom duplex offers the perfect blend of comfort and convenience nestled in the delightful town of Cape Charles. Whether you're in town to soak up the sun at the beach or simply unwind, this property is designed to suit every aspect of your leisurely needs!

Step inside to discover a cozy atmosphere with well-appointed spaces that promise a homely feel from the moment you walk in. The primary bedroom, a restful retreat, along with two additional amply-sized bedrooms, ensures everyone has their personal space. Entertaining? The open-concept living area present the ideal setting for creating memories with loved ones.

Forget about the hassle of street parking; this house comes with its very own off-street parking spots. And for those who can't bear to leave their furry friends behind, you'll be pleased to know this home is pet friendly!

Just a short stroll away lies Central Park, where you can enjoy everything from a peaceful morning jog to a lively afternoon picnic. Need to pick up some essentials or a quick snack? There are many conveniences in town, or the grocery store is just a little over 2 miles away—talk about convenient shopping!

Whether you're looking for a calming weekend getaway or seeking a serene place to call home for a while, this house ticks all the boxes for a laid-back yet vibrant living experience. Book your stay, pack your bags, and prepare to relax—your beachside vacation awaits!

Located right next door to this beautiful duplex is "Seaside". Larger group? Bring along your friends and family and rent both units! 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation. 

- This property is pet friendly for an additional fee (NO CATS). The pet fee is $150 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.

 

Teal Lighthouse

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Internet

Welcome to your next island escape — "Teal Lighthouse"! This lovingly decorated two-bedroom, two-and-a-half-bathroom townhouse proves that you don't need to break the bank to live the coastal dream. Every corner of this charming retreat reflects the creative spirit of Chincoteague Island, with local artist's touches woven throughout that give each room its own personality and warmth.

The primary suite offers a private balcony and bathroom sanctuary where you can unwind after sun-soaked days exploring everything this magical island has to offer. Clean, cute, and effortlessly inviting, this townhouse strikes the perfect balance between cozy comfort and coastal style.

Speaking of exploration, the location here is truly something special. Lace up your sneakers and stroll to the nearby Bay to Beach Trail access point for morning walks surrounded by natural beauty. Feeling adventurous? Maui Jack's Waterpark is just a short distance away, delivering splashy thrills for the whole family. And when the ocean calls — because it always does — the legendary Assateague Beach awaits, complete with wild ponies and endless stretches of pristine shoreline.

Situated conveniently near Beach Road, you'll find yourself surrounded by fantastic restaurants, eclectic shopping, and the laid-back island atmosphere that makes Chincoteague Island one of Coastal Virginia's most beloved destinations.

- 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.

Lighthouse View

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water Access
Pet Friendly
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 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. 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.

Counting Corks

3 Bedrooms
2 Baths
6 Guests
Cape Charles
Waterfront
Pet Friendly
Boat Dock
Internet
Outdoor Shower

Welcome to 'Counting Corks' (formerly known as 'Smith Beach Pines'), the moment you step foot in this beautiful waterfront cottage you feel at home. The pet friendly cottage is 1,150 sq ft, featuring 3 bedrooms and 2 full baths. The primary bedroom has a king size bed and TV. On the other end of the home the second bedroom features a queen bed and a TV. The third bedroom features a twin over a full bunk bed. The cottage also has a bar room leading into the deck area, with plenty of seating to entertain. The dock leads to the creek and is just waiting for you to go crabbing, fishing, or kayaking or simply enjoy the beautiful sunrise while drinking a cup of coffee. The property is a short distance to the community beach and to the community boat ramp. Also features an outdoor shower and a firepit area with plenty of seating. The cottage is located just a few short miles from the Historic Town of Cape Charles and about 25 minutes from Kiptopeke State Park.

- Linens and towels are included with your reservation. 

- No smoking is permitted on the premises. 

- This property is pet friendly with an additional fee of $150 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.

Wildflower

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

Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is a second screened porch overlooking that water from the great room. The second level has a large waterfront master suite with a private balcony, two more bedrooms and another full bath. Close to Memorial Park right across the street from a family restaurant! (Spiral staircase in home, may not be suitable for small children.) For larger groups for family reunions, check out nearby Moon Rising or Herbie's Hideaway!

- 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.

Heron's Hideaway

3 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover your perfect family retreat at this charming three-bedroom, two-bathroom house nestled in peaceful Oyster Bay II on Chincoteague Island. 'Heron's Hideaway' welcomes up to 12 guests, making it ideal for multi-generational gatherings, friend reunions, or anyone seeking a memorable coastal escape.

The heart of this home lies in its thoughtfully designed layout, offering both communal spaces for togetherness and quiet nooks for those precious moments of solitude. Fall in love with the screened-in porch—your new favorite spot for morning coffee, afternoon board games, or listening to gentle summer rain. When you're ready for fresh air and broader views, head upstairs to the deck where peaceful vistas and cooling breezes create the perfect setting for birdwatching or evening stargazing.

The well-appointed kitchen makes meal preparation a pleasure with its dual-oven electric stove, elegant granite countertops, and full-size appliances. Families will appreciate thoughtful touches like the provided high chair, pack-n-play, and collection of board games suitable for all ages.

Located in a tranquil residential neighborhood, this trusted vacation favorite sits at the end of a quiet cul-de-sac, surrounded by lush trees and natural landscaping that creates a beautifully secluded atmosphere. You'll feel worlds away from everyday stress while remaining just a short drive from Assateague Wildlife Refuge, pristine beaches, local restaurants, and charming shops. Remote workers will appreciate the private business nook complete with desk and monitor, allowing you to balance productivity with relaxation. Since 2018, this beloved hideaway has hosted everything from girls' weekends and holiday celebrations, to hunting expeditions and peaceful solo retreats.

Whether you're seeking adventure at nearby Maui Jack's Waterpark, exploring Waterfront Park, or simply enjoying the serenity of island life, this exceptional rental offers the perfect base for your Chincoteague "home away from home" experience.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Pets are permitted with an additional fee. Limit of two dogs only. All pets must be disclosed. 

- 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.

Grandview

4 Bedrooms
4 Baths
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Internet
Outdoor Shower

Enjoy stunning sunsets from this 5 star home at water's edge. Relax with the amazing water view from the north side of the island. Every bedroom is a suite, to ensure all of the adults have the right amount of privacy and a quiet place to stow away with a book. The dining area is big enough to accommodate large family dinners and the kitchen has been newly remodeled and upgraded! With a breakfast bar and wide open living area, you can be sure to have lasting family moments together. Have your cameras ready to capture the changing tides, wildlife and those crazy family moments that are sure to happen in this lovely home. Grandview offers every amenity from a screened porch, an open deck, long pier with a dock, ceiling fans throughout, wireless internet and much much more! This home also includes the use of 2 kayaks.

- 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. 

- 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.

Modest Junxtion

3 Bedrooms
2 Baths
6 Guests
Cape Charles
Charcoal Grill
Internet

Nestled in the heart of historic Cape Charles, this meticulously renovated family residence stands as a testament to thoughtful design and artistic vision. Originally conceived as a duplex, this home has been masterfully transformed into a spacious single-family haven, where European sophistication meets coastal charm.

The first floor unfolds with an open-concept design, anchored by a gourmet kitchen that would delight any culinary enthusiast. Equipped with premium appliances and an impressive array of cooking accessories, including three distinct coffee-making options, the space beckons both casual cooks and seasoned chefs. The dining area comfortably seats eight, while a cozy coffee nook and music corner, complete with guitars and microphones, add playful touches to the living space. Through elegant French doors, discover an entertainment room featuring a carefully curated vinyl collection for music aficionados.

Ascending to the second floor, two identical queen bedrooms offer serene retreats, while the California king guest room provides a luxurious escape with its distinguished wingback chair and footstool arrangement. A dedicated study space ensures connectivity with fiber optic internet, perfect for remote work or planning your next coastal adventure. The crown jewel of the upper level is the remarkably spacious family bathroom, spanning 250 square feet of pure indulgence.

The outdoor space embraces coastal living with a welcoming front porch, expansive deck, and thoughtful amenities including a fire pit, and grill area. The corner lot location provides ample street parking, accommodating boats and extra vehicles with ease.

This home's proximity to Cape Charles' treasured attractions enhances its appeal, with the historic district and beautiful beachfront just moments away. A decade of careful curation by its overseas owners has infused this residence with a distinctive London-inspired aesthetic, creating an unexpected and delightful fusion of sophisticated urban style and relaxed coastal living.

- 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.

Eastside Escape

4 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Town & Country
Gas Grill
Screened Porch
Internet

Discover the perfect blend of comfort, convenience, and coastal charm at 'Eastside Escape', a beautifully updated vacation home ideally located in the center of Chincoteague Island. Whether you’re here for wild pony sightings, beach days on Assateague, or simply to unwind in a peaceful seaside town, this home offers the ideal setting for your getaway!

Step inside and you’ll find a bright, welcoming interior designed for relaxation. The cozy living area invites you to kick back after a day of exploring, while the fully equipped kitchen makes it easy to prepare your favorite meals. Thoughtful touches throughout the home provide the comfort of modern amenities with the warmth of traditional island style.

Featuring four spacious bedrooms and two full bathrooms, this home provides plenty of room for families, couples, or small groups—offering privacy and comfort for everyone in your group. The outdoor space is just as inviting: enjoy morning coffee on the porch, gather for an evening barbecue, or unwind under the stars after a day at the beach.

Conveniently located on Church Street, you’re moments from everything that makes Chincoteague special: charming downtown shops, cafés, and restaurants; the waterfront and iconic sunsets; bike paths and nature trails; Assateague National Seashore with its beaches and wild ponies, and so much more!

Whether you’re seeking relaxation, adventure, or a little of both, 'Eastside Escape' offers the perfect home base for your island getaway. Book your stay today and experience the magic of Chincoteague—from a home that feels like your own.

- 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.

Channel Winds

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

Welcome to your dream island getaway on Chincoteague Island! This waterfront townhouse sits right on the Assateague Channel, serving up jaw-dropping views of the lighthouse that'll make your morning coffee taste even better.

With three bedrooms and two and a half bathrooms, there's plenty of room for the whole crew. The primary en suite bedroom is the real showstopper here, featuring a private balcony that overlooks the water. Imagine waking up, stepping outside, and watching the sun paint the channel gold. Not a bad way to start the day, right?

The outdoor living space is where the magic really happens. Two levels of waterside decks give you plenty of room to spread out, soak up the views, and just breathe. Fire up the gas grill for a seafood cookout while the kids explore, or simply kick back and watch the boats drift by. Life moves a little slower here, and that's exactly the point.

Adventure seekers, this one's for you. Kayaks, a paddle board, and bicycles are all provided, so you can hit the water or cruise the island without packing extra gear. The famous Assateague Wildlife Refuge and its stunning beach are just a short trip away, perfect for spotting wild ponies and catching some waves.

Right around the corner, you'll find Veteran's Memorial Park with a playground, tennis courts, basketball, and more to keep everyone entertained. Need groceries? Island Foods is a quick ride up the road. And for some splashy fun, Maui Jack's Waterpark is nearby too.

This is island living at its finest. Don't let this one slip away, book your island vacation 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.

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