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Langtree

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

Your home away from home... enjoy the water views, bring your boat and use your own dock, or just relax and listen to the whispering pines. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV, and PET FRIENDLY! Great views of Oyster Bay from the front and back decks, and there's a large screened porch for outdoor enjoyment. On the lower (first level) of the home you'll find a large open room with a Queen and 2 Twin beds, as well as a large utility room and bathroom with shower. The main living level (second level) of the home features the living room, kitchen & dining area, as well as 3 bedrooms (K/K/Q) and 2 full bathrooms. Note: This property has a 7 night minimum stay during all seasons.

-Parking only for 4-5 Cars

- 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. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. 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.

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.

Heron's Cove On Salt Meadow

4 Bedrooms
5 Baths
12 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Peaceful and stunning waterfront home! Located on a quiet side-street, Heron's Cove features a reverse floor plan with all bedrooms on the first floor, and the main living-level on the second floor. This allows you to capture and maximize the fabulous bay views! The second floor also features a great room with cathedral ceilings, fully equipped kitchen, gas fireplace and screened gazebo. In addition, there's multiple open decks and a shared dock (with Egret's Cove) into Little Oyster Bay. There are three bedrooms that each have a king size bed, and one bedroom that has two sets of bunk beds. Each bedroom has a private bath. Luxurious comfort while surrounded by Chincoteague's natural beauty and wildlife! Floor Plan: Downstairs (first level) features 4 bedrooms, all with attached private bathrooms. Two of the downstairs bedrooms and the sitting area have private waterside balconies. Upstairs features an open floor plan with the kitchen, living room and dining area. There is also a full bathroom (shower only) upstairs.

- 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.

Cedar Cove

3 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Waterfront
Gas Grill
Internet
Outdoor Shower

Tranquility meets you at every turn at Cedar Cove, a custom-built waterfront home nestled amongst the pines in the Oyster Bay I community. The open floor plan allows for a bright and airy atmosphere in the common areas downstairs - an open living room with a gas fireplace to warm a chilly evening, and a bright and cheery fully-equipped kitchen. The primary bedroom is also found on the ground floor, with a queen bed and bath, flat-screen television, and private balcony overlooking the backyard and waterfront view. The bathroom also has an entrance from the entrance hall of the house, allowing it to act as a bathroom for guests downstairs as well. Upstairs you'll find a game loft complete with a foosball table, a futon, and plenty of board games to keep the kids busy on a rainy day. Two additional bedrooms are also upstairs, one with two full size beds and another with a queen size bed - both have televisions and balconies as well. A newly-remodeled full bath is also located upstairs off the loft area as well. Outside you'll find ample space for plenty of outdoor enjoyment with the family - a spacious deck with outdoor seating and dining areas, a firepit with comfortable Adirondack chairs, and an outdoor shower to rinse off the sand after a long day at the beach. Located in a quiet private community just off the "beaten path" - all the amenities Chincoteague has to offer are just minutes away on the bike or in the car. Bring your kayaks and launch right from the small dock located on the property, or grab a pack of chicken necks at the grocery store and catch a few crabs - round out the meal with a sack of oysters from Gary Howard's market just up the street (if all else fails he sells crabs at a reasonable price too). Then take the time to gather with family on the porch to enjoy the bounty the island has to offer - all from the comfort of Cedar Cove here on Chincoteague Island.

- 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.

Ryokan

4 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Waterfront
Gas Grill
Internet
Outdoor Shower

Welcome to The Ryokan- a quiet refuge that has everything you need for a relaxing vacation. Offering an unobstructed panoramic view of Oyster Bay, this waterfront home is ideal for daytime birdwatching and nighttime stargazing. Bring fishing poles, crab pots, kayaks or paddle boards to use along the bulkhead or put in your boat from the convenient community boat launch. You will only be a short drive or fun bicycle ride away from Assateague Wildlife Refuge, the beach and Main Street of Chincoteague.

There are many features of The Ryokan to ensure a pleasant stay. The split level design offers a full bath and 3 bedrooms upstairs, two of which are waterfront with balconies. Enjoy the beautiful water view from a spacious main floor kitchen and living room. Early birds will love having coffee watching the sunrise from the deck or screened in porch! Downstairs offers a waterside deck as well as a large family room, bedroom with bunk beds and a full bath. Go under the house for a shaded spot to hang your hammock and enjoy an outdoor shower after a day at the beach!

Located in the ever-popular Oyster Bay 1 community, this home is truly an experience for the nature and island lover. We hope you will find The Ryokan a place to return to year after year.

Please note:

- This home does NOT have a washer and dryer on the premises.

- 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.

June's Retreat

4 Bedrooms
5 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

June's Retreat is Chincoteague Island's premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms with floor-to-ceiling windows to the expansive wrap-around verandas, you'll feel as though you're one with nature and your surroundings. Downstairs features a chef's quality kitchen, private billiards room, waterside glass atrium, living room, private den, formal dining room, sitting room and a bathroom. Upstairs you'll find 4 bedrooms with bathrooms (en suite), a sitting area and balcony. The panoramic views of Chincoteague Bay are unobstructed and unsurpassed. Come and see for yourself; we promise you won't be disappointed!

- 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.

Bay Haven

3 Bedrooms
2 Baths & 1 Half
6 Guests
Captain's Cove
Waterfront
Boat Dock
Pool
Internet

Ever dreamed of a home where water views greet you from literally every room? This contemporary three-bedroom, two-and-a-half-bathroom house turns that daydream into your everyday reality, blending sleek modern design with the kind of relaxed waterfront rhythm that's tough to beat.

Walk through the door and the open floor plan immediately shows off, letting light and shimmering water views flow freely from one space to the next. Whether you're whipping up dinner, sprawling on the couch, or catching up with family, the sparkle of the water stays in view the entire time. It's the sort of layout that makes hosting feel effortless and lazy days feel downright luxurious.

Three comfortable bedrooms give everyone space to spread out, with the primary bedroom carving out a peaceful spot to recharge. The contemporary finishes lend a crisp, current feel throughout, so the whole place reads clean and bright.

Then there's the neighborhood, and Captain's Cove genuinely delivers. Think swimming pools, a fitness center, a playground for the little ones, golf for the swing enthusiasts, an on-site restaurant, and a marina for boat lovers. It's practically a vacation resort you get to call home away from home.

When wanderlust strikes, adventure sits close by. Maui Jack's Waterpark brings splashy thrills, the legendary Assateague Beach offers wild ponies and endless beach shoreline, and the boardwalk buzz of Ocean City is an easy day trip away.

Ready to live where the water never leaves your sight? Book your vacation today.

- 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. 

Shore Thing On Oyster Bay

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

Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms on the first level and your main living area on the second level. The great room opens to the kitchen and features wood floors throughout. And the views are spectacular! Lots of windows!! Some of the bedrooms have waterside balconies. This home has four televisions- all with cable hooked up! You'll find all the bells and whistles here! So take a look at all the pictures and then give us a call or book online. Make memories to last a lifetime!

- 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.

Windshadow

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

You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining area. Walk through the French doors off the living room to a large screened porch and sky deck overlooking the Chincoteague Bay. There is a first floor King bedroom with en-suite bath and two twin bedrooms on the second level. Windshadow is a premier PET FRIENDLY vacation rental.

- 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: 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.

Avalon

4 Bedrooms
2 Baths & 1 Half
10 Guests
Chincoteague Island
Waterfront
Screened Porch
Internet
Outdoor Shower

Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a large great room that boasts two family rooms, a dining area and large kitchen. From the gas fireplace, to the 16' cathedral knotted pine ceilings, this home is bright, warm and inviting. Avalon offers two queen bedrooms with screened porch access (one private) and two twin bedrooms. Offering over 600 sq. ft. of screened porch - you could live outdoors! The first level also offers a full size futon and 1/2 bath. Avalon is one of our most popular offerings; it books quickly! 

- 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.

Conch Shell

3 Bedrooms
1 Bath
6 Guests
Chincoteague Island
Waterfront
Internet
Outdoor Shower

The house is located on Pine Drive in Piney Island - the closest neighborhood to the beach - convenient for shopping and dining on Maddox Blvd. This wonderful waterfront beach bungalow features a wrap around deck with views of Assateague and the light house. You can bring your boat, jet skis or kayaks and keep them tied up out front. There is a spacious living room for entertaining and a nicely remodeled kitchen! Your rental also includes water access to a tidal creek that comes up from Oyster Bay - it's a great place for the kids to crab or to launch a kayak or canoe. 

- 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.

Our Happy Place

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Discover your own piece of paradise at this incredible beach getaway! 'Our Happy Place' is the perfect retreat for up to 7 guests seeking comfortable, tastefully decorated accommodations. This cozy vacation home is clean, simple, and fully furnished, including amenities that will make you feel right at home. Even your furry, 4-legged family members can join in on the fun, small to medium dogs are welcome.

Situated in the desirable Oyster Bay I waterfront community, 'Our Happy Place' is located at the end of a wide-mouth canal, offering unobstructed water views and a private dock platform. You'll love the convenience of being situated next to the community boat ramp, making it easy to launch your watercraft for a day of adventure.

Relax and unwind on the expansive wrap-around screened porch overlooking the water, featuring plenty of comfortable seating and a dining area. Savor your morning coffee or sip a cool drink after a day at the beach.

'Our Happy Place' is a single-level home with 3 cozy bedrooms that can accommodate up to 7 guests. The bedrooms include 1 queen, 2 twins, and 1 bunk bed (twin over double). There are 2 full bathrooms, one of which is a tub shower combo.

- 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.

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