Home Vacation Rentals By Owner In Chincoteague Island, VA

Showing 80 Of 307 Vacation Rentals
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Exceptional(31)

$378.28

/ Nightly
Private Vacation Home

Cedar Cove | Oyster Bay Waterfront Home w/ Gas Fireplace, Dock, Firepit, Deck & Outdoor Shower

Chincoteague Island, Virginia, United States

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.brbr- No smoking is permitted on the premises. br- Linens and towels are included with your reservation.br- No pets are permitted on the premises.br- 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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Exceptional(5)

$426.98

/ Nightly
Private Vacation Home

Vineyard Cove by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Ocean air, salty hair, not a care, take me there……brbrLife is so busy - our days are filled with one commitment after another. Isn’t it time for a Beach Break - time to reconnect and rejuvenate with those who matter most If you can make the time, we have the perfect Vacation Destination for you at Vineyard Cove on Chincoteague Island….brbrVineyard Cove sits directly on the Chincoteague Bay in the prestigious Wildcat Community on the North end of our beautiful Little Island by the Sea. You’ll feel a million miles away from the real world, yet still be only a few minutes from everywhere you want to be! Assateague National Seashore is less than 10 minutes away - home of our famous Wild Ponies, and you’re a hop, skip, and jump away from fabulous Shops and Dining, as well as Historic Downtown Main Street. brbrAhhh, Waterfront Living - just imagine waking each morning to Herons, Eagles, and Egrets dancing over the Bay while you enjoy your morning coffee - it’s pure heaven. Grab a cocktail in the evening and wander to the end of your Private Pier to take in magnificent Sunsets - there are 2 comfy Adirondacks just waiting for you. And, your family will fall in love with fishing and crabbing right in your own backyard! brbrAs you enter this amazing home, either via the front door or the Ramp that leads to the back Deck, you’ll know right away that this is a HOME - not just a house. The care and love that has gone into Vineyard Cove spans generations, and it’s something you can feel. brbrYou’ll love relaxing in the Living Area that lines the front of the Vineyard Cove with Free WiFi and Flat Screen Roku TV. Sink into the oversized Sectional Sofa and share stories of the day’s adventures, or curl up with a good book. Decorated with a gorgeous Coastal Flair, the colors of sand and sea, along with a Shiplap Wall, create that island vibe we all love so much. brbrWandering through the French Doors, you’ll find a Family Room with lovely Views and a cozy Fireplace for those chilly Off Season Stays. We just love this home’s layout - there’s room for everyone to spend time together without ever feeling crowded, and when you need a little “me-time”, there’s plenty of spaces perfect for that, as well! Grab a cup of coffee from the Coffee Bar, and head out to the huge Deck, or slip to the Gazebo to kick back and listen to the Tree Frogs Sing. brbrThe Family Room opens to the well-stocked Kitchen and Dining Area. Between the Dining Table, Kitchen Island, and Bistro Table, there’s room for all to dine in the comfort of Central AC, or head out to the Deck to dine Al-Fresco with a Water View! Mealtime will be a bay breeze in this gorgeous Kitchen with beachy white cabinetry and stunning aqua Backsplash reminiscent of sea glass found along the Beach. There’s a convenient Half Bath down the Hall, which also houses a Laundry Closet with Full Size Washer and Dryer. brbrVineyard Cove sleeps 8 in pure comfort and style. On the 1st Floor, you’ll find Bedroom 1 with a comfy Queen Bed and Flat Screen TV. With Coastal Bedding and warm Oak Furniture, it’s so warm and inviting. The Private Master Bath has a Garden Tub/Shower. brbrHeading upstairs, you’ll find yet another Living Area beautifully decorated, which also has a Full Sleeper Sofa. Right next door is Bedroom 2, which is bright and cheerful and has a Full Bed. brbrDown the Hall, you’ll find Bedroom 3, dressed in blues and tans, also with a Full Bed. A 2nd Full Bath with a Tub/Shower Combo is in the Hall. brbrAs you can see, Vineyard Cove is so much more than just a place to lay your head each night. This fabulous home is a true Vacation Experience, both inside and outside. And oh, the memories you’ll make in this very special place. Plan your escape to Chincoteague Island and Vineyard Cove today!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
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Exceptional(7)

$388.84

/ Nightly
Private Vacation Home

Ryokan | Unobstructed Oyster Bay Waterfront Views w/ Screened Porch, Balconies & Boat Launch Access

Chincoteague Island, Virginia, United States

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.brbrThere 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!brbr​​​​​​​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.brbrPlease note:br- This home does NOT have a washer and dryer on the premises.br- Linens and towels are included with your reservation.br- No smoking is permitted on the premises.br- No pets are permitted on the premises.br- 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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Sleep 12

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Exceptional(51)

$337.75

/ Nightly
Private Vacation Home

Smooth Sailing by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Smooth Sailing - Work like a Captain, but Play like a Pirate....br br We cannot control the wind, but we can direct the sail - Life is busy. It gets more and more difficult to find that cherished time with family & friends. This is the sole purpose of Smooth Sailing on Chincoteague Island. It is a retreat. A destination. A place to rejuvenate and reconnect with those who matter the most. This wonderful Home was created for just that.br br Located in exclusive Oyster Bay, Smooth Sailing is in the heart of the island, yet feels a million miles away. Surrounded by Whispering Pines and located directly on the Canal, its serenity will embrace you even as you pull into the driveway. This fabulous Home makes the most of both Outdoors Living & Indoor Comfort. With 3 Bedrooms and 2 Full Baths, it sleeps 8 more than comfortably. Before you even enter the house, you'll want to run to the backyard and take in those Views and that Salty, Sweet Bay Breeze. br br Upon entering Smooth Sailing through the fabulous & beautifully decorated Screened Porch, you're already thinking what a great place this would be to sneak away with a good book. Opening the door, the Soaring Ceiling & Wall of Windows to the Water are simply stunning. This Home is both open & cozy at the same time. The Living Room features an oversized Sectional Sofa you'll love sinking into after a fun-filled day on the Beach, Flat Screen Cable TV, and of course, Free WiFi. Light, bright, and beachy with colors of Sand & Sea throughout, you can relax and still take in the Water Views from the huge windows. br br The Open Floor Plan at Smooth Sailing is perfect for gathering and entertaining. The Living Area opens to the spacious Dining Area & Kitchen, with plenty of room for all at the Dining Table and Breakfast Bar. Even the Chef in the family can take in fabulous views while preparing the Fresh Catch of the Day. Dine indoors in the Central AC or Al-Fresco on the Waterfront Deck, while listening to the Tree Frogs. br br Also on the 1st Floor are 2 Bedrooms and a Full Bath with Tub/Shower Combo. Bedroom 1 has 2 comfy Twin Beds and a Twin Trundle. Adorned in Nautical Navy with a fun Whale Theme, it 's just a great place to spend time. Right next door is Bedroom 2, with a Queen Bed, decorated with a Nautical Flair. You'll love the Custom Tilework in the Full Bath, which is convenient to both the Living Area and Bedrooms. Follow the Warm Wood Railing upstairs, and you'll fine a Loft overlooking the Living Area, as well as the Master Bedroom with luxurious King Bed and Flat Screen TV. The Master Bath has a Walk-in Shower and lovely vanity.br br If the Indoor Living at Smooth Sailing isn't enough, just wait until you check out the backyard, aka Paradise. Being directly on the Canal certainly has its advantages. The kids (and the kid in you) will delight in fishing and crabbing right from your Private Dock. Bring your Kayaks and launch them in the calm canal water. Don't have kayaks Let us know and we can help you arrange to have them delivered when you arrive. With a depth of roughly 2 1/2 feet, feel free to bring your boat! Direct access to the Bay is right at the end of the canal - the flounder are waiting for you! And there's nothing better than relaxing in the Swing under the house with a glass of wine as the sun sets. Just pure paradise.....what are YOU waiting for br br Smooth Sailing - Catch the Wind in your Sails. Explore. Dream. Discover. br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.
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Sleep 8

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Exceptional(45)

$219.78

/ Nightly
Private Vacation Home

Charming Island Beach House by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Rhythm and Blues - The Ocean's Roar is Music to the Soul.....br br br You know that favorite song that just stays with you - the one you long to hear again and again This is the feeling you will get while staying at Rhythm & Blues on beautiful Chincoteague Island. Tucked away on the East Side, this Charming Chalet will steal your heart. Located only steps from the Public Boat Launch & amazing Views of the Assateague Lighthouse, Rhythm & Blues is the perfect place for kayakers, boaters, & nature lovers. As you turn down Pointer Lane and see Rhythm & Blues nestled in the whispering Pines, you'll know you're in for a very special Vacation Experience. Traveling with a large family or several families together Be sure to check out her Sister House, Les Bon Temps, right next door - the perfect way to have lots of togetherness, while still having privacy.br br Park the car and leave your worries at the end of the quaint boardwalk leading to the house - you won't be needing them here. This rustic, yet modern, dream home has 3 Bedrooms and 2 Full Baths, and sleeps 7 more than comfortably. As you enter through the Screened Porch, you're already thinking about how good some Local Crabs or our Famous Chincoteague Oysters are going to taste out there on a warm summer evening.br br The warmth that exudes from Rhythm & Blues is simply magical. With Soaring Ceilings and rich Knotty Pine Barn Wood, you won't ever want to leave. The Living Area has comfy furniture perfect for sinking into after a fun-filled day on the Beach - relax and enjoy the Free WiFi while cooling off in the Central AC. There is even a Cozy Fireplace for those chilly off-season stays. The well-stocked Kitchen will please the Chef in your family, and has all you need to make meal time super easy. Dine indoors, or Al-Fresco on that awesome Screened Porch. The huge Front Deck is the perfect place to sip your morning coffee and listen to the birds play over the water, just at the end of Pointer Lane. br br Also on the 1st Floor are 2 Bedrooms - Bedroom 1 is perfect for the kids, and features a Pyramid Bunk and Flat Screen TV. With sunny yellow walls, lots of games, and even a kids-table, they will entertain themselves for hours. Bedroom 2, right next door, is adorned in colors of Sea Grass & Sand Dunes, and has a Queen Bed. A Full Bath with Tub/Shower Combo is shared on the 1st Floor. br br Wander up the stairs and you won't believe your eyes - the huge Loft with a Wall of Windows is simply stunning. Sink into the oversized Sectional Sofa while taking in the Views, or catch a movie on the Flat Screen Cable Smart TV with DVD Player. This is just an awesome space to relax in and catch up with family and friends. French Doors lead from the Loft to the spacious Master Bedroom with King Bed, Sitting Area, and Master Bath. The Master Bedroom Fireplace adds an especially romantic touch - what a great way to end the day. The Master Bath is bright and sunny with a Skylight and Tub/Shower Combo.br br The Outdoor Living Space is every bit as wonderful at Rhythm & Blues. Toast marshmallows and share stories of the day's adventures around the large Shared Fire Pit. Sister House, Les Bon Temps, is right next door - together these 2 homes will sleep 13 people! At the end of Pointer Lane, you can easily launch your kayaks or small boat, as well, and catch crabs right off the dock. The calm waters on the East Side are perfect for kayaking and fishing, and you can kayak across the Channel to see our famous Wild Ponies on Assateague as they graze in the Marsh - a breathtaking experience.br br Much like Music & Rhythm, Chincoteague Island and Rhythm & Blues will find their way into the secret places of your soul.br br Rhythm & Blues - Let the Sea set you free.....br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.
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Sleep 7

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Exceptional(3)

$244.5

/ Nightly
Condo

Beachy Place by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Have you always wanted to vacation on Chincoteague Island, but couldn't bear the thought of 5 of you in a hotel room Love the idea of a Vacation Home, but don't want to break the bank Look no further than Newly Renovated ‘Beachy Place’ at Sea Tag Lodge, sitting directly on the Assateague Channel! The Sea Tag Lodge has been helping families make amazing memories for decades, and is tucked on the ever-popular East Side of Chincoteague Island - peaceful and captivating. These adorable Condos offer some of the most breathtaking Views to be had. Just imagine relaxing on your Waterfront Balcony and seeing our famous Wild Ponies roaming in the Marsh across the Channel. There is something for absolutely everyone in your family at Beachy Place!brbrBeachy Place, which is Condo #11, has been totally renovated, and is decorated with a serene Coastal Flair we just know you’ll love. Conveniently located on the 1st Floor with parking just steps away, it’s perfect for those not wanting to deal with a ton of stairs. You’ll love kicking back in the Living Area and enjoying Free WiFi and Flat Screen Smart TV after a day of searching for our famous Wild Ponies at Assateague - which, by the way, is just down the street! Or slip out to your Waterfront Wonderland and sip Sweet Tea in a comfy Adirondack, as you watch Herons, Eagles, and Egrets fish for their morning meal. And keep your eye out for Wild Ponies across Channel, grazing in the Marshes, as they are a frequent sight!brbrThere’s no need to cook out everyday when you have a Kitchen like this - beachy cabinetry, Stainless Appliances, and tons of work space - and we just love that backsplash! Dine in the comfort of Central AC, or at the water’s edge at your private Picnic Table, and take in that salty, sweet sea breeze. Hopefully you will be cooking up some fresh fish, crabs, or clams you caught right from the Community Dock! A Charcoal Grill is also provided in the picnic area if grilling is your thing. And since Beachy Place is on the ground level, you can walk directly out your back door and enjoy kayaking, boating, crabbing, and more!brbrThe Master Bedroom features a King Bed, another large Flat Screen Smart TV, and is beautifully dressed in nautical navy and crisp white. Bedroom 2, which is how you’ll enter Beachy Place, has a Pyramid Bunk (Twin over Full), and a delightful beachy vibe. Sea Tag Lodge has on-site Pay Laundry for your convenience, as well. brbrBeachy Place also comes with a Private Boat Slip that will accommodate up to a 25 foot boat! And if you happen to be coming for our famous Chincoteague Pony Swim, you truly cannot ask for a better location - you won't even have to leave your Balcony! Traveling with friends or extended family Check out Sunrise Sonata and Sunrise Serenade - you can rent all 3 and enjoy having everyone in the same location! brbrSeaside Vacations does not allow group rentals to guests under age 25. NO SMOKING AND NO PETS. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Building has Exterior Security Cameras. For safety and insurance reasons, the storage or charging of electric bikes (E-Bikes) or E-Bike Batteries is strictly prohibited inside the unit, on balconies, patriots, or in any common area associated with this property with exception of the bike rack. Guests are not permitted to bring e-bikes or e-bike batteries into the unit or to charge them using any outlet or power source on the premises. Violation may result in immediate termination of the rental agreement.
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Sleep 6

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Exceptional(50)

$270.97

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Private Vacation Home

Charming island cottage by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Les Bon Temps - Good Times & Beach Vibes....br br Les Bon Temps loosely translates to Let the good times roll - can you think of a better phrase to kick off your Chincoteague Island Vacation this year Tucked away on the East Side, this quintessential Chincoteague Cottage is beyond charming. Located only steps from the Public Boat Launch & amazing Views of the Assateague Lighthouse, Les Bon Temps is the perfect place for kayakers, boaters, & nature lovers. Traveling with a large family or several families together Be sure to check out her Sister House, Rhythm & Blues, right next door - the perfect way to have lots of togetherness, while still having privacy.br br Life at Les Bon Temps is truly laid back.....relax on the Deck and take in those salty, sweet bay breezes. There's nothing like the smell of Low Tide on our little piece of Paradise. Stroll down to the end of the drive to take in astonishing Bay and Assateague Lighthouse Views, and it's an easy walk to very popular Memorial Park. Bring your kayaks or small boat to drop in at the Community Boat Launch just across the street and paddle out to explore one of our Sand Bars or do some fishing. Don't have kayaks No worries, we are here to help you plan your Chincoteague Adventures - just give us a call!br br As you enter Les Bon Temps, you'll pass through a delightful Sunroom adorned Beachy Reds & Blues. This is a great place to sip your morning coffee or gather at the end of the day to share stories of the day's adventures. Walking into the Living Area, you'll be amazed at how light, bright, & spacious this beautiful Vacation Home is. Soaring Warm Wood Ceilings and a carefree Open Floor Plan welcome you and let you know right away what a fabulous stay you're about to have. br br Relax after a fun-filled day of exploring Assateague, sink into the comfy Living Room Furniture, and enjoy the Flat Screen Cable TV and Free WiFi. There is even a cozy Fireplace for taking the chill out of those off-season visits - one of our favorite times on the Island! The Living Area opens to the huge Kitchen with Dining Area. There is plenty of room at the Dining Table for all, and the Chef in your family will love preparing meals in this very Well-Stocked Kitchen. You can even grill the Fresh Catch of the Day and dine Al-Fresco on the Deck. br br Les Bon Temps sleeps 6 very comfortably with 3 Bedrooms and 2 Full Baths. The theme throughout this breathtaking home is pure fun - enjoy life to the fullest and make every moment count. That's easy to do here on our little slice of heaven. In Bedroom 1, you'll find 2 Twin Beds and soothing colors of Sea Grass & Nautical Navy. Down the hall, Bedroom 2, which is the Master, has a fabulous Queen Bed and lots of space. You'll love the Master Bath with Tub/Shower Combo. The Lofty Warm Wood Ceiling makes this space feel enormous. Just across the hall, Bedroom 3 has another Queen Bed and is beautifully decorated with Bold Reds and Beachy Blues. There is another Full Bath with a Tub/Shower Combo conveniently located down the hall, as well. br br The Outdoor Living Space is every bit as wonderful at Les Bon Temps. Toast marshmallows and share fish tales around the large Shared Fire Pit. Wander down to the Boat Launch and try your hand at crabbing or fishing. Sister House, Rhythm & Blues, is right next door - together these 2 homes will sleep 13 people, making it a wonderful choice for several families traveling together or a family reunion. Time shared around the Fire Pit is sure to make some awesome new Vacation Memories for all!br br Life is short - Les Bon Temps - Let the Good Times Roll right here on Chincoteague Island!br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.
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Exceptional(90)

$317.57

/ Nightly
Private Vacation Home

Stunning Chincoteague home minutes from the beach by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Ariel's Grotto - A True Beauty at the Beach br br The welcome mat is out at spectacular Ariel's Grotto - only minutes from Assateague National Seashore, home of the Famous Wild Ponies! This 3 Bedroom/2.5 Bath Home is simply stunning. Located on a very quiet street mid-island, this awesome Chincoteague Vacation Home is sure to make all of your Vacation Dreams come true!br br As you enter this Coastal Cape, you will feel as if you stepped into Coastal Style Magazine. Cool colors of Sand & Sea welcome you, with hints of fun Nautical Red throughout. The spacious Foyer is a great place to kick off your shoes and leave your worries by the door - you won't be needing them during your time here on our Island! br br Ariel's Grotto opens to Soaring Ceilings and tons of glorious Natural Light. This home was designed with Easy Beach Living in mind. The gleaming Bamboo Floors and pale Blue Walls instantly make you feel at ease! You'll love relaxing in the huge Living Area with Cable TV and Free WiFi. An oversized sectional sofa ensures there is room for all, and there is even a Fireplace to take the chill off those Off-Season Evenings. What a great place to curl up with a good book or get lost in a movie with the family, and the Owners have thoughtfully provided books, games, and movies for your enjoyment!br br Just around the bend you will find the spacious Dining Area with seating for 6 to 8, which opens to the Gourmet Kitchen. There is also seating at the Breakfast Bar for quick meals before hitting the Beach. Ariel's Grotto has a great set-up for the Chef in your family with tons of countertop space, a Cook Top Island, every gadget imaginable, and beautiful Tile Flooring. The whimsical Coastal Decor and gorgeous Sea Green Walls make it a wonderful place to sip a glass of wine while whipping up some fresh Local Chincoteague Seafood! Is the weather too nice to dine indoors Just a few steps off the Kitchen, gorgeous French Doors open to a huge Screened-in Porch with Dining Table. Listen to the trees rustle in the salty air and take it all in. A Gas Grill is provided on the Patio just off the Porch for grilling some burgers, or maybe that Flounder you caught Surf Fishing!br br Ariel's Grotto has a convenient 1st Floor Master Bedroom with Master Bath, featuring a brand new King Bed and more fabulous colors that just make you happy to be there. This offers privacy for Mom and Dad, or is handy if someone in your group prefers not to use the stairs. There is a Walk-in Shower Combo in the Bathroom and lots of storage. Also on the 1st Floor is a Half Bath that is adjacent to the Kitchen and Living Area!br br As you wander upstairs, you'll find 2 more Bedrooms with charming Beachy Decor. Bedroom 2 features 2 Queen Beds, a TV, and lots of space. The Nautical Theme and Blue Walls will make you feel as if you never left the Beach. Bedroom 3 has a Twin Bed with handy Twin Trundle Bed. Ariel's Grotto comfortably sleeps 8 people in total luxury and serenity. There is a 2nd Full Bathroom upstairs also with a Tub/Shower Combo and cheerful Surfer Theme.br br Chincoteague Island has been voted Happiest Seaside Town and Best Small Beach Town, just to name a few accolades. You will not find huge, commercialized Boardwalks and high-rise buildings, but you will find peace, nature, tranquility, and ponies at their very finest. Enjoy one of our famous Nature Boat Tours, go fishing and clamming, relax on the Beach with your loved ones, or go exploring on one of Assateague's Hiking Trails - maybe even climb to the top of our famous Lighthouse! Whatever you enjoy most, Ariel's Grotto is the perfect Home Base for your Chincoteague Island Adventures!br br Ariel's Grotto - Where your Chincoteague Vacation Story Begins.....br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.
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Exceptional(33)

$284.94

/ Nightly
Private Vacation Home

Happy Pines by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Happy Pines - Refresh, Renew, & Reconnectbr br As you turn onto Pine Creek Drive, you will feel the hustle & bustle of the busy world melt away. Happy Pines is located near the end of this quiet street, nestled in a Pine Grove, and surrounded by beautiful trees and Beach Grasses. This lovely 3 Bedroom, 2 Bath Vacation Home is in THE perfect place - walking distance to the famous Carnival Grounds and everywhere you want to be, yet you will feel a million miles away. It is a wonderful combination of convenience and serenity. With a layout suitable for one family or two small families, this awesome home is definitely the place to be for your Chincoteague Island Vacation.br br The warm and inviting Living Area with Gleaming Floors, Cozy Fireplace, Free WiFi, and huge Flat Screen Cable HDTV is a wonderful place to relax after a day of exploring the Beach and Assateague Island. Sink into the oversized, comfy furniture and share stories of the day's adventures and Wild Ponies. A wall of windows lets in glorious Natural Light and adds to the beauty of this Classic Home. Decorated with a Coastal Theme throughout, you will love the Local Art and pictures taken by the Owners themselves of their many beautiful Chincoteague Island memories. br br Just around the corner, you will find Happy Pines has a large Dining Area that opens to the equally large Kitchen. There is seating for 6 at the Dining Table and 3 at the super-handy Breakfast Bar. The Kitchen is very well-stocked with all you need to make family meals a bay breeze. With rich Wood Cabinets, tons of Counter space, and every gadget you could possibly need, the Chef in your family will love cooking up some fresh Chincoteague Seafood here - or grilling some burgers on the Charcoal Grill! Not one to cook on vacation No worries, you are a hop, skip, and jump away from many of our fabulous Local Restaurants. Just off the Dining Area is a spacious Screened-in Porch with comfortable furniture and Ceiling Fan overlooking the secluded Backyard. Just imagine relaxing here with your morning coffee and taking in that salty, sweet air. Wander upstairs to the Rooftop Deck and you will wonder why you never noticed how many stars really are in the sky.br br Happy Pines has 3 Roomy Bedrooms and 2 Full Baths. The Master Bedroom, adorned in Nautical Navy and Sandy tones, has a Queen Bed and Flat Screen Cable TV. The Master Bath is delightful with Beachy Blue Walls, a large Walk-in Shower, and a window to let in those sea breezes and natural light. Bedroom 2 has a Queen Bed and is accented with colors of Fresh Lime and Navy Blue. Bedroom 3 features 2 Twins - a great room for the kids! A 2nd Full Bathroom with a Tub/Shower Combo is shared between these rooms. There is also a Queen Sleeper Sofa in the Living Area!br br At Happy Pines, the Outdoor Living is as wonderful as the Indoor Living. The spacious and private Backyard is a great place to throw a Frisbee with the kids, play some Bocce Ball, or just chase Lightning Bugs. That is what this time is about, right Relaxing, reconnecting, discovering, playing......ahhhh, the simple pleasures that are Chincoteague Island and Happy Pines. br br Happy Pines - Relax. Unwind. Get in a Flip Flop state of mind. br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.
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Sleep 8

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Exceptional(56)

$335.24

/ Nightly
Private Vacation Home

A 'Teague of Our Own | Walk to Downtown, Dog Friendly Home w/ Fireplace & Enclosed Porch

Chincoteague Island, Virginia, United States

Welcome to A 'Teague of Our Own! This in-town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated in 'beachy-chic' decor! The living room has abundant seating, complete with a flat screen TV and electric fireplace for those off-season stays. The kitchen is stocked to a chef's standards - there's nothing you won't find including a gas stove, sharp knifes and an herb garden. The three bedrooms are upstairs, and the full bathroom (tub and shower) is downstairs. The enclosed porch with sliding windows allow for room to spread out in any weather. Large carport to keep a vehicle and all your gear under cover. A huge yard for cookouts, games and showering in the outdoor Tiki-shower. This fabulous vacation home truly has it all and has become one of our most popular rental homes. Don't delay; book today! brbr- No smoking is permitted on the premises. br- Linens and towels are included with your reservation. br- 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. Pet restriction: limited to one small dog only.br- 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.
Bed 3

Bed

Bath 1

Bath

Sleep 8

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Exceptional(41)

$263.52

/ Nightly
Private Vacation Home

Gone Coastal | Channel Breezes, Porches, Walk to Downtown & Maddox, Pet Friendly

Chincoteague Island, Virginia, United States

Enjoy the cool breezes coming off the Chincoteague Channel while relaxing on the porch at Gone Coastal! Nestled in a grove of pines and tucked just off East Side Drive, this charming unit has everything your family desires for a wonderful stay on Chincoteague Island. Bright and cheery nautical decor will help to put you on island time. Featuring two bedrooms, two and a half baths, a spacious living and dining area, and a fully-equipped kitchen. The two bedrooms are on the upper level. The master features a full bed with flat screen television, full bath, and balcony with sliding door and comfortable outdoor furnishings. An additional bedroom featuring a full size bed and double bunk, and a full bath is located in the hallway upstairs as well. On the ground floor you'll find a spacious living area with large flat screen tv, plush seating, and plenty of reading material. The eat-in kitchen features everything you'll need to prepare and enjoy meals at home - electric range, roomy refrigerator, dishwasher, coffee bar, and dining table. A full-sized washer and dryer are located in a utility closet just off the kitchen, and a barbecue grill is located on the back porch for your convenience. Located centrally on the island - you're a quick bike ride or easy walking distance to the commerce on Maddox Boulevard or downtown Main Street, or to Memorial Park located just down Eastside Drive. Pop into one the oyster farms and grab a sack to bring back and enjoy with a glass of wine as the sun sets on another day Gone Coastal. Please Note: No boats or trailers are allowed at the complex.brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. br- 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. br- 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.
Bed 2

Bed

Bath 2

Bath

Sleep 6

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Exceptional(6)

$338.16

/ Nightly
Private Vacation Home

Pony Paradise by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Are you all about ponies in paradise If so, you will love comfy and cozy ‘Pony Paradise’ in the very heart of Chincoteague Island! Formerly ever-popular ‘Sunshine and Daydreams’, this Seaside Vacations’ fan-favorite is under New Ownership, and y’all are going to LOVE what they’ve done with the place! This adorable 3 Bedroom/2 Full Bath Cottage is located on Willow Street, just across from where our famous Wild Ponies are penned at the Carnival Grounds. Stroll to the Carnival weekends in July, the Historic Downtown District to shops and dining, or just skip across the street with your morning coffee to watch the ponies graze. What makes vacationing at Pony Paradise even more fun You get to bring your favorite pup along with a $100 pet fee (Limit 2)! Your pup will especially appreciate the Fully Fenced-in yard for him to play safely in!brbrPony Paradise has packed a lot of bang into your vacation buck. As you enter through the Screened Front Porch, you’re already thinking you’ll never want to leave. Just imagine curling up here with a good book and taking in that salty, sweet bay bay breeze. Watch the Ponies grazing just across the Street, and you can even enjoy your 4th of July Fireworks right from your Screened Porch!brbrUpon entering Pony Paradise, you’ll be warmly welcomed by serene Colors of Sand and Sea - just breathtaking. With gorgeous flooring reminiscent of a stroll on the Boardwalk and bright and beachy furnishings, you may never want to leave. There’s even a cozy Fireplace for those chilly off-season stays - one of our very favorite times on our Island. You’ll love relaxing after a fun-filled day exploring Assateague in the Living Area with Free WiFi and Flat Screen Streaming TV. There’s plenty of room for all to stretch out, yet still be together.brbrThe Chef in your family will love the spacious Eat-in Kitchen with both a Breakfast Bar and Dining Table. Well-stocked with all you need - even a Waffle Maker - mealtime will be no chore. You can grill the Fresh Catch of the Day - which hopefully you caught - out back, while listening to the Tree Frogs sing. Dine indoors in the comfort of the AC, or wander to one of many great Restaurants nearby. After dinner, slip out to the back Deck to take in that salty, sweet sea breeze, or gather around the fire pit in the backyard and share stories of the day’s adventures. The spacious yard has two sections, with one that is fenced-in, making it just perfect for your furbaby to get some much needed exercise.brbrPony Paradise sleeps 7 in total comfort and style. The Master Bedroom, with a Queen Bed, is dressed in beach blues and crisp whites. The Private Master Bath has a huge Vanity and Walk-in Shower. Down the Hall, Bedroom 2 has a Full Bed and is inviting with cheerful Lime and Vanilla - just like a piece of Key Lime Pie. Bedroom 3 is perfect for the kiddos with Twin Bunk Beds and sleeps 2. A Roll-a-way Twin Bed is available for the 7th member of your family. A 2nd Full Bath with a Tub/Shower Combo is shared. And while no one likes doing laundry while on vacation, the Full Size Washer and Dryer will sure come in handy.brbrLINENS NOT INCLUDED, BUT LINEN RENTAL IS AVAILABLE. brbrFriendly dogs welcome with $100 Pet Fee. Max 2 Dogs with Permission. Dogs MUST be current on Flea/Tick Preventative and Immunizations. No Cats.brbrEvery effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
Bed 3

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Bath 2

Bath

Sleep 7

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Exceptional(12)

$355.99

/ Nightly
Private Vacation Home

Saltwater Pony by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Welcome to Saltwater Pony - Beach Mode activated!brbrHave you been longing for a Beach Vacation that is truly easy-breezy Clear your calendar and grab those who matter most, because we’ve got you covered with this gorgeous Custom Home in the very heart of Chincoteague Island! Saltwater Pony is tucked on Ridge Road - close to everywhere you want to be - including in the path of the Pony Parade during our Annual Pony Swim - and is almost Brand New! Only a few minutes from Assateague National Seashore, where our famous Wild Ponies roam free, there’s so much to do. Whether you enjoy fishing and crabbing, sunbathing, or shell-combing, you’re sure to find our slice of heaven to be pure paradise!brbrAs you pull up to Saltwater Pony, you’re welcomed by its charming Coastal Style - the Covered Porch beckons you to sit a spell and sip Sweet Tea, as you watch our Little Island by the Sea come to life each morning. With plenty of parking and all the bells and whistles, you’ve got the makings of an amazing Chincoteague Vacation.brbrSaltwater Pony is the perfect combination of contemporary style and comfort, with the warmth and charm of beach house living. Upon entering, you’ll be swept away by cool grays and whites, and beachy flooring, reminiscent of a stroll on the boardwalk. Kick off your flip flops and let the fun begin!brbrYou’ll love kicking back in the Living Area with Free WiFi and Flat Screen Streaming TV. Saltwater Pony’s open layout is perfect for spending time together without ever feeling crowded. There’s even a cozy wall-mounted Fireplace for ambiance on those chilly off-season stays. With multiple Sitting Areas, everyone can find their comfy place, whether enjoying a movie, or curling up with a good book. A convenient Half Bath is just off the Living Area. brbrThe Chef in your family will adore the gorgeous Kitchen with Stainless Appliances and gleaming Quartz Countertops. Well stocked with all the comforts of home, there’s no need to eat out everyday - unless you want to, that is! Dine in the comfort of Central AC in the Dining Area, or wander out to the Screened Porch to dine Al-Fresco while listening to the Tree Frogs sing. In the backyard, there’s also a Picnic Table perfect for enjoying some Fresh Local Crabs and Chincoteague Oysters, or whipping up some burgers on the Gas Grill. brbrSaltwater Pony is beautifully designed to sleep 8 in 3 Bedrooms - 2 are Masters - and with 3 Full Baths, plus the Half Bath! Bedroom 1 is on the 1st Floor, perfect for those not crazy about stairs. Dressed in beachy blues and soothing grays, it has a luxurious King Bed, Flat Screen Streaming TV, and beachy white furnishings. The Attached Master Bath has a crisp feel with a Quartz Vanity and Tub/Shower Combo. brbrWandering upstairs, we just love the Sitting Area at the top of the landing - grab a good book and find a little time for yourself. Bedroom 2 is just perfect for the kiddos with a Pyramid Bunk (Twin over Full) with a Twin Trundle, and sleeps 4. Between the Foosball Table, Games and Legos, Mini Chess Table, and Flat Screen TV, there’s plenty to keep them entertained! There’s a Full Bath in the Hall with a Tub/Shower Combo. brbrBedroom 3 is another Master with a comfy King Bed, elegant grays and whites, and Flat Screen TV. There’s a Twin Sleeper Chair, which could come in handy for a little one that doesn’t want to sleep far from their parents. There’s a Workstation if you have to catch up on a few emails, as well. The Attached Master Bath again has a Quartz Vanity, but this time has a Walk-in Shower. Also on this floor, you’ll find the Laundry - perfectly located between the Bedrooms - with a Full Size Washer and Dryer for your convenience. brbrAs if all of this wasn’t enough, let’s chat about the Outdoor Living at Saltwater Pony! We just love the spacious yard - plenty of space to run and play. Gather around the Fire Pit at night to toast marshmallows and just BE together. There’s also an Outdoor Shower for rinsing off sandy feet after a day at the Beach. brbrSo, if you’re looking for a true Vacation Experience, where the only worries you’ll have is how to squeeze all of the magic in, book your time in fabulous Saltwater Pony today!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements.
Bed 3

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Bath 3

Bath

Sleep 8

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Exceptional(4)

$363.9

/ Nightly
Private Vacation Home

The Sea Horse | Spacious Family Home w/ Screened Porch, Fenced Yard, Beachy-Chic & Pet Friendly

Chincoteague Island, Virginia, United States

We are pleased to offer 'The Sea Horse'! This fabulous home features a spacious, open floor plan with room for the whole family - and even the furry family members! The grand room downstairs features an open kitchen and dining space with center island, and the living room with large windows that allow natural lighting. There are French doors that open up to the wonderful screened porch - perfect for enjoying morning coffee or cool drinks after a day at the beach! To compliment the outdoor space, there's a fenced yard that's perfect for the pup! The master bedroom (King bed) with en suite bathroom, as well as a second bedroom (Twin bed) and full bathroom complete the downstairs space. Upstairs is where you'll 2 more sleeping areas/bedrooms - one with a Queen bed and the other with 2 sets of bunk beds (Twin over Full each). Clean, modern and comfortable, you're sure to love all that 'The Sea Horse' has to offer. From the beachy-chic decor and design, to the fully stocked kitchen and open spaces, there's nothing left undone. Come and see for yourself!brbr- Linens and towels are included with your reservation.br- No smoking is permitted on the premises. br- 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. Pet restriction: two pet max.br- 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.
Bed 4

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Bath 2

Bath

Sleep 10

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Exceptional(23)

$283.24

/ Nightly
Private Vacation Home

The C-Ray Cottage by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

The C-Ray Cottage - Life is better with a little sand between your toes.......br br We are big believers that every Home has a story.......a story rich in happiness and sadness, struggles and successes - that creates its very essence. The C-Ray Cottage has a story you will love.......br br This adorable Bayfront Waterman's Cottage exudes that quintessential Chincoteague Charm. The C-Ray Cottage is the former working office of C. Ray Jester, a Chincoteague Original, who was the owner and manager of Jester Bros. Oyster Company. Born in 1892, he began working the water at an early age - seeding & growing Chincoteague salt oysters. By 1925, C. Ray had a fleet of 3 boats, and was operating the oyster shucking and canning operation here.br br Ray worked in this €˜cottage€™ office and on the water until he had a massive heart attack in 1953. Luckily he survived, but could no longer work the business. He enjoyed his later years with his family €“ 2 children, 6 grandchildren, and 9 great-grandchildren until his death in 1971. He would be pleased to know that one of his great-grandsons has followed in the family footsteps - Dan Davis of Captain Dan€™s Tours is considered one of the best and most knowledgeable tour guides on the island! For more information about the Jester family and their history of working the water, please visit Dan€™s page.br br While you€™re here on the island, you may notice that the Cottage is not in the architectural style of most homes on Chincoteague. That€™s because Ray had the cottage moved to Chincoteague from Hog Island in the €˜20s, along with other structures that he had purchased. The C-Ray cottage originally sat on the other side of the larger lot, next to the water and near the street. It was moved one last time to this position in 1971 by the Owner's grandfather, Bill Jester, who then built his own retirement home next door.br br The C-Ray Cottage has everything you need for a fabulous Chincoteague Experience. Located on the water's edge, the Cottage has incredible Bay Views - the perfect spot to take in our famous Chincoteague Sunsets with a glass of Pinot. Comfortably sleeping 4 with 2 Bedrooms and 1 Bath, it's just perfect for a small family or romantic getaway. Relax on the huge Screened Porch that lines the front of the Home, or take in Sea Breezes on the Waterfront Screened Porch. br br The comfortable Living Area has been recently updated with lovely furniture for relaxing, New Flat Screen Cable TV, and Free WiFi. The C-Ray captures everything you love about a bygone era, with all of the modern amenities you want and need. The well-stocked Kitchen will please the chef in the family and has all you need to make mealtime a bay breeze. Just imagine grilling the fresh catch of the day on the Charcoal Grill. You can also walk to many wonderful restaurants, as The C-Ray is in an awesome Main Street location, including The Island Creamery and Mr. Whippy! And to make life even easier, the TickTown Trolley stop is just across the street. br br The Master Bedroom is serene with Tropical Colors,a comfy Queen Bed, and a 2nd New Flat Screen TV. Just off the Master, Bedroom 2 has a Twin Bed with Twin Trundle - a perfect room for the kids. There is also a super convenient Washer & Dryer housed here. The cozy Full Bath with Tub/Shower Combo is shared between the Bedrooms. br br Well-appointed, amazing views, AND this incredible Cottage only has a 3 Night Minimum all season. Are you ready to make lasting Chincoteague Island Memories br br The C-Ray Cottage - Give me the Sea and a little Cottage just to be.......br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Please note that The C-Ray Cottage has 6 ft. ceilings in the bathroom. Taller than that Call us - we can help!
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

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