Vacation Rentals By Owner In Chincoteague Island, VA

$381.53

Sunset Bay Villa 116 | Ground-Floor Marina Walk-Out, Pool + Spa Bath Luxury Villa

Chincoteague Island, Virginia, United States

A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy tiled shower and whirlpool bath. Villa 116 will sleep 8 (beds for 6 plus a queen size air mattress), and includes a full laundry, all appliances, a gourmet kitchen, and more. There's also a pool and fitness room for your enjoyment! Tastefully furnished, you can relax, enjoy and entertain your family and friends in style. | NOTE: This unit does not have a boat slip, however, use of the marina is included. brbr- 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.

Bed

Bath

Sleeps

$561.55

/ Nightly

Private Vacation Home

Grey Heron | Waterfront Home w/ Dock, Kayak Launch, Screened Porch, Epic Sunsets & Pet Friendly

Chincoteague Island, Virginia, United States

Majestic views await you from every room at Grey Heron, a charming raised contemporary located on North Main Street. Enjoy the unparalleled island sunsets from the private dock, spacious screened in porch and dining area, or with it's floor to ceiling windows and numerous cozy seating areas - from anywhere else in the home! Vintage artwork from local artist Hall Lott, known for his cover artwork for the Chincoteague Island Easter & Decoy Festival and Pony Swim posters, adorn the walls at every turn. Plush, cozy furniture in the living area as well as a round-about room featuring stunning 180-degree views of Chincoteague Bay and salt marsh give you plenty of space to enjoy company comfortably. A fully equipped kitchen (range, dishwasher, refrigerator) to prepare meals for family and friends, which is connected to the great room featuring a beautiful working fireplace and natural wooden floors. Grey Heron features 3 bedrooms, each boasting their own private balcony. On the upper level (accessible by the spiral staircase in the great room) you'll find the master bedroom - with the largest balcony, overlooking the sweeping vista of the bay and marsh. A comfortable king sized bed and television, as well as a full bath. The floor to ceiling bay window delivers plenty of natural island sunshine into the bedroom. Downstairs you will find the other two bedrooms - both with queen sized beds, a small balcony, and a cozy sitting area with view of the bay and marsh. Bring your bushel basket and crab right off the dock, then enjoy the bounty of the Chincoteague Bay from the screened-in porch. Bring your kayaks as well and launch them right from the private launch found off the bulkhead on the property. An outdoor shower to hose off after a sandy day at the beach. Plenty of space outside to enjoy family activities, and pet-friendly so bring your furry friends - they love basking in the sun on the dock as much as people do!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

Bath

Sleeps

$394.14

/ Nightly

Private Vacation Home

Donovan's Reef | Colorful Downtown Chincoteague Cottage w/ Sunroom, Walk to Shops & Pet Friendly

Chincoteague Island, Virginia, United States

Charming Chincoteague coastal cottage doesn't even begin to describe this place, but it's a start. Cheery, bright, and colorful - with some form of island history gracing every nook and cranny. Find the perfect mix of old and new in this unique home. Close enough to the main drag on Maddox Boulevard and Main Street - but out of the hurly-burly here on Ocean Boulevard. Wake up a few minutes before everyone else and head across the street to get fresh donuts from Mister Whippy or chocolate croissants from Amarin to surprise everyone with. You'll be the hero for the day, until someone else brings home oysters that night. Oh, and bring your furry friends along, because this one's PET FRIENDLY! This property features lots of nooks for sleeping spaces - a loft upstairs, featuring skylights that let the bright island sunshine flood in. Up here you'll find a cozy king size bed in one room, and two twins in another, with a full bath that features a gorgeous tiled stand up shower. Downstairs you'll find two more bedrooms - one with two twins, and the other with a king. Three different comfortable living areas, one of which is an outdoor sunroom - and that room has doors that connects to the downstairs king - in addition to the main living area. Small backyard area for letting the puppies play or eating lunch outside at the picnic table. The retro mid-century kitchen has everything you'll need to prepare that island seafood dinner with what you catch down at the town dock, and a lovely dining area to enjoy it as a family. Donovan's Reef is located in the heart of downtown Chincoteague, allowing you an easy walk to all the shopping the island has to offer. Stop by Chincotiki on your way home and grab an orange crush or two!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

Bath

Sleeps

$275.18

/ Nightly

Private Vacation Home

Daisey Cottage | Remodeled Ridge Road Retreat Near Downtown w/ Patio, Fenced Yard & Pet Friendly

Chincoteague Island, Virginia, United States

Come visit Chincoteague Island and stay in this adorable coastal cottage with your family. Lovingly remodeled and updated, this charmer located on Ridge Road is sure to book up fast! Close enough to hustle and bustle of carnival and downtown, but far enough away to enjoy some peace and quiet - you'll find all the comforts of home at Daisey Cottage. Upon entering you'll be greeted by a comfortable living area with television. Skylights to let in a ton of natural light, letting you bask in island sunshine. A cute kitchen featuring everything (electric range, fridge, dishwasher, coffee maker) you'll need to make a family meal, if you're heart so desires. A bright and cheery open dining area is connected to the kitchen - allowing you to chat while preparing meals or snacks. A full bathroom. A utility closet with washer and dryer. Two bedrooms - the master with a queen and television. And the second bedroom boasts a bunk that has a full on the bottom and a twin on the top - how fun is that ! Bring your bikes and ride down to Memorial Park for a little fishing or crabbing. Outside you'll find a cute patio area with sitting area, as well as a small fenced in area that is perfect for your four legged friends to enjoy while you're outside as well. Daisey Cottage is pet-friendly, all members of the family are welcome - book today!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

Bath

Sleeps

$269.39

/ Nightly

Private Vacation Home

Channel Lookout | Memorial Park Water Views w/ Private Deck, Assateague Channel Scenery & Fishing

Chincoteague Island, Virginia, United States

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

Bed

Bath

Sleeps

$543.6

/ Nightly

Private Vacation Home

Blue Pointe Bayside | Cul-de-Sac Waterfront w/ 4 Decks, Screened Porch, Sunsets & Bay Views

Chincoteague Island, Virginia, United States

Spectacular waterfront home on the end of a cul-de-sac! Bright, airy and immaculate! Four decks, including one off of the stunning 2nd floor Private Master Suite. Dramatic cathedral ceiling in the cozy, waterfront living room. A screened porch to host an outdoor dinner. Central heat for those off-season stays, and Central A/C for the summer stays, make this the perfect vacation house all year 'round. A sunny, well equipped, eat in kitchen for the gourmet cook. Down-draft cook top and gas grill; perfect for any meal. Beautiful sunsets on the Chincoteague Bay - Water views from every room! Large, hot water outside shower and an oyster shell path to the water so you can easily walk out to the bay to crab, fish and kayak.brbr- 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.

3

Bed

3

Bath

8

Sleeps

$567.41

/ Nightly

Private Vacation Home

Relax Inn by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Welcome to Relax Inn — where the days move a little slower, the laughter lingers a little longer, and the moments become memories you’ll carry home.brbrBrand New in 2025, Relax Inn oozes Southern Hospitality and is absolutely stunning. Tucked on a quiet Lane off the beaten path, you’ll feel a million miles away from the real world, yet still be close to everywhere you want to be, including Assateague National Seashore and Chincoteague Wildlife Refuge - where our famous Wild Ponies roam free. You're even just a short stroll from the Chincoteague Carnival Grounds. And if you’re looking to accommodate a large group or family reunion, Nestled Inn, Relax Inn, and The Feathered Nest are all tucked in this wonderfully quiet location! Relax Inn sits tucked behind Nestled Inn, and has beautiful wooded views. brbrThe Living Area, dressed in beachy blues, is the perfect place to gather and spend time together after a day of searching for Wild Ponies, fishing, or just sunbathing. Sink into the oversize sectional and enjoy family movie night together, or hang out on the Screened Porch and share stories of the day’s adventures. The open layout at this gorgeous home is perfect for spending time together without ever feeling crowded. brbrJust off the Living Area, the Kitchen will delight the Chef in your family. Mealtime will be anything but a chore in this well-equipped Kitchen with all the comforts of home, and then some! We love the combo of beachy white cabinetry and flooring reminiscent of a stroll on a rustic boardwalk. Add in Stainless Appliances and a beautiful Tile Backsplash, and Relax Inn is utterly perfect. Grab a quick bite at the Breakfast Bar before hitting the beach, or dine Al-Fresco on the awesome Screened Porch, which is furnished with furniture for both dining and relaxing. Not one to cook on vacation We’ve got you covered! You’re less than 5 minutes away from several great dining venues!brbrAfter dinner, check out the Patio with Fire Pit, roast some marshmallows, and make memories sure to be shared for generations to come. After all, isn’t this what life is about brbrRelax Inn sleeps 8 comfortably in 4 Bedrooms, and with 3 Full Baths. Bedroom 1 is a desirable 1st Floor Primary Bedroom with a luxurious King Bed, Flat Screen Smart TV, and is dressed in nautical navy and sea salt. The Attached Primary Bath has a Double Vanity and Custom Walk-in Shower. Bedroom 2 is also perfectly situated on the 1st Floor, and has a comfy Queen Bed, Flat Screen Smart TV, and sunny yellows and warm grays. While there is not an Attached Bath, the Full Bath with Walk-in Shower is just across the hall, and also convenient to the Living Area.brbrWandering upstairs, you’ll find 2 more Bedrooms, a Full Bath in the hall, and a huge Bonus Room. The Bonus Room will be a favorite of the kiddos with Flat Screen Smart TV and giant Bean Bag Chairs. Bedrooms 3 and 4 are equally gorgeous with a Queen Bed and Flat Screen Smart TV in each Bedroom. A 3rd Full Bath is in the hall and has a Tub/Shower Combo.brbrAll of this, and keep in mind you’re only a short ride away from one of the most pristine beaches in America. Whether your pleasure is sunbathing, fishing, shell combing, or searching for Ponies, our pristine beaches offer something for everyone! Relax Inn for the win on Chincoteague Island!brbrNO SMOKING AND NO PETS. Seaside 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.

Bed

Bath

Sleeps

$343.38

/ Nightly

Private Vacation Home

Teal Cottage by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Collect Memories, not things…..brbrLife is busy - crazy busy! Work, school, meetings, sports - and repeat. Precious moments together that used to be easy to find, are hard to come by these days. This is why we must MAKE them happen! So, clear the calendar and grab those who matter most - we’ve got the Vacation of a lifetime for you right here on Chincoteague Island at beautiful Teal Cottage!brbrTeal Cottage is the epitome of the Vacation Dream Home - gorgeous Coastal Colors and Decor, a fabulous Location perched on a serene Pond, beautifully Appointed, and you’ll even have Views of the Assateague Channel! Tucked at the end of a quiet street in ever-popular Oyster Bay II, this home truly has it all. And Oyster Bay II is a fan-favorite with quiet streets perfect for walking or bike riding, and is lined with whispering pines.brbrHaving made amazing memories here on our Little Island by the Sea themselves, the Owners of Teal Cottage named this special home after their love of the Waterfowl that live right in the Pond, and her Grandmother’s love of this bright and beachy color. And now Teal Cottage is ready to make your time on Chincoteague special.brbrYou’ll love sinking into the comfy Sectional in the Living Area after a fun-filled day exploring Assateague, and enjoying Free WiFi and Flat Screen Streaming TV. With gleaming Hardwood Floors and tons of Natural Light, Teal Cottage is so warm and welcoming.brbrJust off the Living Area, the Well-Equipped Kitchen is sure to please with Granite Countertops, Stainless Appliances, and both a Breakfast Bar and an Island! Mealtime will be a sea breeze with every gadget imaginable. Dine in the comfort of Central AC in the spacious Dining Area, or Al-Fresco on the Screened Porch with amazing Views. Down in the yard by the water’s edge is yet another Picnic Area - perfect for enjoying some Fresh Local Crabs - and there’s even a Fire Pit!brbrTeal Cottage sleeps 10 in pure luxury and style. The Master Bedroom has a desirable 1st Floor Location with a comfy Queen Bed and Private Access to the Water View Deck. In the Private Master Bath, you’ll find a Double Vanity and Walk-in Shower. The Laundry Area and another Full Bath with Walk-in Shower are conveniently located down the Hall, just off the Kitchen.brbrWandering upstairs, you’ll discover 2 more beachy and beautiful Bedrooms, an Office Nook, and another Full Bath with Tub/Shower Combo. Bedroom 2 has another Queen Bed, and just wait til you open the Private Door leading to the Upper Deck - WOW, those Views! Kick back and enjoy a glass of Wine while taking in Views of the Pond and Assateague Channel - you’ll never want to leave this spot! Down the Hall, Bedroom 3 sleeps 6 with 2 sets of Pyramid Bunks (Twin over Full) and Flat Screen Streaming TV. Need to do a little work while you’re here The Office Nook is perfect for that, and you even get to work with spectacular Water Views.brbrLife is all about Experiences, and that is exactly what Teal Cottage has in store for you - so much more than just a place to lay your head at night! Traveling with another family or planning a bit of a reunion Barefoot Breeze is right next door - book both to double the fun!brbrOccupancy of 10 is strictly enforced! Seaside 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.

Bed

Bath

Sleeps

$172.94

/ Nightly

Private Vacation Home

Sun Singer - 2BR townhome, Waterview shared pier,deck -Pet friendly NO LINENS

Chincoteague Island, Virginia, United States

Amenities: Central A/C, 2 Smart TVs (bring your own login info for Prime, Netflix and Hulu), Bluetooth Speaker, WiFi, Microwave, Dishwasher, W/D, 2 Decks, Charcoal Grill, Shared Crabbing Pier, Open Outside Shower (hot and cold), Allows Dogs OnlybrbrLovely Pet Friendly Townhouse located near the water. Enjoy the community pier or sit and relish in the beautiful views of the channel. This 2 bedroom, 2 and a half bath property provides everything you need for a pleasant and relaxing vacation. brbrTHIS HOUSE DOES NOT PROVIDE LINENS AND TOWELS. PLEASE BRING YOUR OWN OR CALL US TO RENT THEM.brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrBed Sizes: 1 Queen and 1 Bunk w/ a Double and a TwinbrbrSunday Changeoverbrbr2026 Prime Season Rate $ 875 per week / $ 125 per night br2026 Off Season Rate $ 651 per week / $ 93 per night 3 night minimumbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Bed

Bath

Sleeps

$354.84

/ Nightly

Private Vacation Home

Amistad by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

The very definition of ‘Amistad’ is friendship - and that suits this beautiful home so well, as you’ll feel like you’re visiting a long, lost friend on our Little Island by the Sea. You’ll love making unforgettable family memories in this charming historic home that has graced Chincoteague Island with its presence since the early 1900’s. With the quintessential Chincoteague Charm you love, plus the modern amenities you want and need, Amistad will treat you to a true island experience without missing any of the conveniences of home! What makes it even sweeter You can bring the whole family - including your family dog - who will absolutely love sunning and playing in the large Fenced Yard!brbrTucked on North Main Street, you’re close to everywhere you want to be, including Assateague National Seashore, where our famous Wild Ponies roam free. Whether you love searching for Ponies, Beach Combing, or Fishing, one of the most gorgeous beaches in our country is just a short drive away! Did you know that Assateague National Seashore is the most visited National Park in our country Spend a little time here and you will discover why this is.....brbrAs you swing open the gate to enter the yard, you’ll be greeted by a large Deck perfect for hanging out and enjoying dinner Al-Fresco, while taking in that salty, sweet sea breeze. Kick off your flip flops, and let the fun begin - you’re on island time now!brbrAmistad has so many nooks and crannies to explore, and all the comforts of home. You’ll love kicking back in the Living Area and enjoying Free WiFi and Flat Screen Streaming Only TV after a fun-filled day at the Beach. The kids will have a blast playing Ping Pong on the large Screened Porch, or hanging on the Upper Deck, which has lovely Water Views. brbrThe Chef in your family will find mealtime to be a bay breeze with the well-stocked Kitchen. Dine in the comfort of Central AC, or outside on the Deck - the world is your oyster at Amistad. Not one to cook on Vacation You are right down the street from some of the best dining on the island including Bill's, Don's Seafood, and more. Just off the Kitchen, you’ll find the Dining Area, and also the Mud Room, which leads to the backyard, and houses a Full Size Washer and Dryer for your convenience. brbrAmistad sleeps 10 people in 4 Bedrooms, plus the Loft, and is perfect for one large family, or 2 small families to share. Bedroom 1 is located on the 1st Floor and has a comfy Queen Bed, Flat Screen Smart TV, and an Attached Full Bath with Tub/Shower Combo. brbrWandering upstairs, Bedroom 2 is dressed in sunny yellows and blues, and has 2 Full Beds. You can also access the Upper Deck through this room - the perfect place to take in amazing Chincoteague Sunsets over the Water. Just across the hall, Bedroom 3 has a Full Bed, and pale greens and blues. On the other side of the hall sits Bedroom 4, which has a Twin Bunk Bed, and sleeps 2. There is also a Sleeper Ottoman in the Living Area that converts to a Twin Bed, just in case you need another option. brbrBut wait - we aren’t done yet! There’s one more special place in Amistad you’re sure to love. Wander up one more flight of stairs to the Loft - the kids will just adore this space. With a Foosball Table, Game Tables, and a King Sleeper Sofa, it’s the perfect hangout! brbrAmistad is in a great location, has tons of space, lots to do, and welcomes your furbaby with a $100 Pet Fee per pet - what more could you want Enjoy everything from swimming, fishing, clamming, or beach-combing to chilling on the porch with a glass of wine while you watch one of our incredible Chincoteague Sunsets. If you truly want to experience Chincoteague Island Life as the Locals do, Amistad should be your first stop.brbrWell-Trained Dogs welcome with $100 Pet Fee each - 3 max, and must be approved in advance. Dogs must be current on Vaccinations, and on Flea/Tick Preventative. Seaside 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. LINENS INCLUDED, NO SMOKING, NO VAPING FAMILIES ONLY AND MUST BE AT LEAST 25.

Bed

Bath

Sleeps

$318.96

/ Nightly

Private Vacation Home

Lily Pad 2 by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

“Not all who wander are lost…..”brbrWelcome to Lily Pad 2 in the very heart of Chincoteague Island! If you’ve been looking for the perfect place to “get lost”, yet still be close to everywhere you want to be, this is the place for you!brbrBrand New Lily Pad 2 sits tucked down a quiet Lane, and is the sister-house to Lily Pad on Wayne Road, sitting almost behind it. This Brand New Construction is not only stunningly beautiful, it sleeps 9 and welcomes your family’s dog! And, you can rent Lily Pad and Lily Pad 2 together to accommodate your large family, or 2 families traveling together, and receive a $100 Discount!brbrYou’ll love Lily Pad 2’s classic Coastal good looks with beachy blues and crisp whites. We also love that you can access the home through the front of the house, or use the ramp on the side, for those who prefer not to use stairs. The Front Porch beckons you to sit a spell and take in that salty, sweet sea breeze…..brbrYou’ll love kicking back in the Living Area and enjoying Free WiFi and Flat Screen Smart TV. Light, bright, and open, there’s plenty of room to spend time together without ever feeling crowded. We love the Colors of Sand and Sea, and the beachy flooring, reminiscent of a stroll on a beach boardwalk.brbrMealtime will be easy-breezy in the Well-Stocked Kitchen with tons of Countertop space and warm Wood Cabinetry. Grill the Fresh Catch of the Day on the Charcoal Grill, and dine in the comfort of Central AC. The Breakfast Bar is perfect for a quick bite before hitting the Beach, and between that and the Dining Table, there’s plenty of room for all.brbrJust off the back of Lily Pad 2, you’ll find an awesome Screened Porch with plenty of comfy seating - the perfect place to begin and end every precious Vacation Day! Your furbaby will love sunning on the porch or in the yard, and there’s even a refreshing Outdoor Shower for rinsing off sandy feet. Take a stroll down the street to take in stunning Views of the Assateague Lighthouse and Channel, plus you’re only a quick drive or bike ride to Assateague National Seashore, where our famous Wild Ponies roam free!brbrThis adorable home sleeps 9 in comfort and style in 3 Bedrooms and 2 Full Baths. Just off the Kitchen, you’ll find the Primary Bedroom with a comfy Queen Bed, Flat Screen Smart TV, and an Attached Full Bath. Decked out in Nautical Navy and Sandy Beige, it’s beautifully furnished. The Attached Full Bath has a gorgeous Navy Double Vanity, and Walk-in Shower. Just outside of the Bedroom, you’ll find a Full Size Washer and Dryer for your convenience, as well as access to the Screened Porch.brbrOn the other side of Lily Pad 2, you’ll find 2 more Bedrooms and a 2nd Full Bath with Tub/Shower Combo. Bedroom 2 has another Queen Bed, while Bedroom 3 sleeps 5 with a Full over Full Bunk Bed, plus a Twin Trundle. A perfect space for the kiddos!brbrLife is short - pack your bags, grab those who matter most, plus the furbabies, on and head on down to Lily Pad 2 on Chincoteague Island for your next Beach Break!brbrFriendly dogs welcome with a $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

Bath

Sleeps

$649.83

/ Nightly

Private Vacation Home

Egret's Cove | Bayfront Oyster Bay Retreat w/ Hot Tub, Screened Porch, Dock & Fenced Yard for Pets

Chincoteague Island, Virginia, United States

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

Bath

Sleeps

$207.02

/ Nightly

Private Vacation Home

Shell of a Time by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Ready to have a ‘Shell of a Time’ on your next trip to our Little Island by the Sea ! You will absolutely fall in love with this beautiful Cottage on Chincoteague Island - tucked on a quiet street, but close to everywhere you want to be! brbrShell of a Time has all that you love about a quintessential Chincoteague Cottage, plus the Modern Amenities you want and need. Newly Renovated, Shell of a Time truly has it all. You’ll love sinking into the huge Sectional in the Living Area and enjoying Flat Screen Streaming TV and Free WiFi after an adventurous day exploring Assateague National Seashore - home of our Famous Wild Ponies! With welcoming Colors and Flooring reminiscent of a stroll on the Boardwalk, you’re sure to feel at home right away!brbrThe Chef in your family will adore the newly renovated Kitchen will all you need and then some! We just love the Metal Backsplash and Black Faucets/Accents - rustic yet modern at the same time. And you can slip out to the Sunroom and dine under the comfort of the shade trees - sooo relaxing. You’ll love grilling the Fresh Catch of the Day,, which with any luck, YOU caught! Not one to cook on Vacation No worries - there are many great options just a hop, skip, or jump away. And don’t forget ending your day with a Sweet Treat from Mr. Whippy’s or The Island Creamery!brbrShell of a Time sleeps 6 in 2 comfortable Bedrooms. The Master has a comfy Queen Bed and is soothing with Colors of Coral and Sea. Right across the Hall, Bedroom 2 sleeps 4 in a very cool Full over Full Bunk Bed - a great space for the kiddos! A bright and beachy Full Bath is shared and has a Tub/Shower Combo. brbrChincoteague Island is all about making family Memories that you’ll treasure forever. Whether you spend the day shellcombing and searching for Ponies, Fishing - either in the Surf or in a Boat, or taking in a spectacular Chincoteague Sunset, this wonderful Vacation Home will make sure you have a Shell of a Time!brbrOccupancy strictly enforced. Seaside 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.

Bed

Bath

Sleeps

$259.01

/ Nightly

Private Vacation Home

Serenity at Deep Hole Hideaway | Cozy Retreat w/ Deck, Firepit, Full Kitchen & Pet Friendly

Chincoteague Island, Virginia, United States

Welcome to your blissful oasis, Serenity at Deep Hole Hideaway! This charming haven has been given a complete makeover to cater to all your vacation dreams. The kitchen is stacked with top-notch gadgets to whip up that perfect meal. The living room features a cozy sleeper sofa to squeeze in a few extra guests. The main bedroom boasts a luxurious queen-sized bed, while the guest room offers a snug twin daybed, providing ample space for up to six guests. Step outside and relax on the deck, indulging in a long-awaited book. And, if you're in the mood for some classic campfire fun, gather around the firepit and toast up some scrumptious S'mores and hotdogs!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

Bath

Sleeps

$260.39

/ Nightly

Private Vacation Home

Escape at Deep Hole Hideaway | Chic 2BR Retreat w/ Full Kitchen, Daybed + Sleeper Sofa, Pet Friendly

Chincoteague Island, Virginia, United States

Enter a world of tranquility at Deep Hole Hideaway! Need a break from the daily grind We've got you covered! Our chic and well-equipped living space will make you feel right at home. And when your tummy rumbles, our kitchen is your culinary sanctuary. Two snug bedrooms await you, furnished with a Queen bed, a Twin daybed, plus a sleeper sofa for your whole posse! The elegant and refreshing décor will overwhelm you with happiness as soon as you step through the front door!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

Bath

Sleeps

$446.04

/ Nightly

Private Vacation Home

Grandma's House | Renovated 4BR w/ First-Floor Suites, Screened Porch, Game Den & Accessible Ramp

Chincoteague Island, Virginia, United States

Introducing a charming and newly renovated home on Chincoteague Island! Grandma's House is a delightful residence, boasting four cozy bedrooms, including two primary bedrooms conveniently located on the first floor, each designed for comfort and ease. With three well-appointed bathrooms, including a walk-in shower, the home is designed to cater to your relaxation and convenience needs. Grandma's House also has a handicap ramp for your convenience!brbrStep into the culinary paradise of a beautifully kitchen, complete with a sleek tiled backsplash, where both seasoned and aspiring chefs can whip up delectable dishes. Connected seamlessly to the dining area, this kitchen is perfect for gatherings and feasts.brbrFamily fun is never in short supply thanks to the inviting den, complete with an air hockey table and darts for a bit of friendly competition. The screened porch offers a breezy retreat for evenings, while the spacious patio is set with both a gas grill and smoker for those sunny weekend barbecues. The heart of this home is undoubtedly its wide-open outdoor space, complete with a basketball hoop for the sports enthusiast and a front deck that invites you to enjoy your coffee while the morning breeze gently brushes against your face.brbrWhether you're entertaining guests or enjoying a quiet afternoon, this home ensures you can make the most of every moment. So come by and see why this isn't just any house — it's a vibrant living space waiting to be called 'home'! Here's a fun bonus — this home is attached to a charming apartment affectionately known as Grandpa's Cottage, which is available as a separate rental. Rent them together for a larger group!brbr- 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.

Bed

Bath

Sleeps

$240.65

/ Nightly

Cottage

Cottage On Famous Chincoteague Island-Famous Wild Ponies

Chincoteague Island, Virginia, United States

Colorful, cute and cozy describe this two bedroom one bath cottage on Chincoteague Island famous for the annual Pony Penning in July. Two bedrooms with queen size beds. Two enclosed porches to relax on and drink your morning coffee. Outside shower offers both HOT and COLD water to use coming home from the beach. Enjoy evening refreshing shower under the stars! Charcoal grill for cooking those nightly summer meals with a drink in hand. Picnic table under shade of tree to enjoy your barbecue. Outdoor furniture to relax, read, and take in beachy breezes or just have a drink, relax and chill out shooting the breeze with friends and family. Four beach chairs provided for your convenience (2 low chairs to sit lower on the sand/beach and 2 captain like chairs-fold up-easy to carry). Air conditioning and ceiling fans. Come explore what the island has to offer and more! See the famous ponies, walk up to the lighthouse for an amazing aerial view of the island. Check out the new water park! A great place for the kids to chill and have fun for the day. Relax and kick back in the beach. Rent bicycles, scooters or kayaks. Take a tour on a boat around the island. Taste some of the best seafood at our many restaurants! Go fishing off the piers or crabbing in the park, or clamming near the beach. Mini golf and more. Check us out for the next rocket launch! Check the Chamber of Commerce or Chincoteague on line for annual Seafood festivals, Blueberry festival, arts and crafts, decoys, and more! So much to do! Come see Chincoteague and Assateague Island!brbrbrACTIVITIES:brbrROCKET LAUNCHES brbrCheck NASA Wallops Island for future rocket launches!brbrbrOTHER EVENTS:brbrMay 4th. 54th Annual Seafood Festival brbrJuly 2024 Pony Penning Swim!brbrJuly 2024 Fireworks At Carnival Grounds brbrOctober 2024 Oyster Festival at Tom’s CovebrbrDecember 2024. Christmas Parade!

Bed

Bath

Sleeps

$407.04

/ Nightly

Private Vacation Home

Canalfront home with Screened Porch by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Freedom - it's a State of Mind. The sense of freedom that comes with being on Vacation is like none other. When was the last time you broke away from the day-to-day with those who matter most Well, the time is now, and the Vacation Destination is Gray Pearl in the heart of Chincoteague Island. This beautiful Canal Front Home is located in prestigious Oyster Bay - serene and peaceful, yet close to everywhere you want to be. With 4 Bedrooms, 2.5 Baths, and a waterfront wonderland in your own backyard, there's no better place to make those amazing Vacation Memories. brbrTucked away on a quiet Canal and surrounded by Whispering Pines, you won't even want to leave the grounds. You will love being able to fish and crab from your own backyard - oh, the wildlife you will see here. Watch Herons and Egrets fish for their morning meal as you relax on the Screened Porch. The wide Canal is perfect for bringing your Boat, Kayaks, or other Water Toys. Don't have kayaks Just let us know and we are happy to help you with that! The calm waters of the Bay are perfect for kayaking, and just at the end of the Canal. There is so much fun to be had without even leaving your yard!brbrGray Pearl is just as stunning on the inside. This huge 3,000 square foot home is light, bright, and spacious. You’ll love kicking back in the Living Area with Free WiFi, Flat Screen Smart TV, and comfy furnishings, after a fun-filled day at the Beach - which, by the way, is less than 10 minutes away! You can take in gorgeous Views - right from the Living Room sofa. The awesome layout of Gray Pearl is perfect for spending time together without ever feeling crowded. With warm wood accents and lots of wonderful natural light, it’s spacious and cozy, all at the same time. brbrThe Chef in your family will love the enormous and well-stocked Kitchen, and the Breakfast Bar is perfect for a quick bite before hitting the Beach. Dining options you ask Dine indoors in the spacious Dining Area, or Al Fresco on the Screened Waterfront Porch while taking in that salty, sweet air. Grab some Fresh Local Seafood from Gary Howard's, just around the corner, and fire up the Gas Grill. With any luck, you'll be steaming some Crabs you caught yourself in the Canal! You are also just a hop, skip, and jump away from some fabulous Chincoteague Restaurants, as well.brbrThis wonderful home sleeps 10 in pure comfort in style with 3 Bedrooms on the 1st Floor, and a huge Bedroom Suite upstairs! Bedroom 1 is the Primary Bedroom and has a luxurious King Bed, and is dressed in beachy blues and whites. The Attached Full Bath has a Walk-in Shower. You also have access to the Waterfront Deck - just imagine slipping out to stargaze while the rest of your family is snoozing…..brbrBedroom 2 is perfect for the kiddos or singles with 2 Twin Beds and lots of closet space. Right next door, Bedroom 3 has a comfy Queen Bed and is bright and beachy. There is a 2nd Full Bath with a Tub/Shower Combo convenient to the Bedrooms and Living Area. brbrWandering upstairs, you’ll find Bedroom 4, which is a huge Bedroom Suite with a Living Area equipped with another Flat Screen TV and lots of comfy furniture. On one side, there is both a Full Bed and a Twin Bed, and on the other side, there is a Twin Daybed, so this room sleeps 4 comfortably, and would make a great area for the kids, or offer privacy for a couple! There is a Half Bath on this level, as well. brbrGray Pearl truly is the perfect blend of fabulous Indoor and Outdoor Living. Spend the days exploring Assateague National Seashore, just a 5 minute drive away, and visit our Famous Wild Ponies, collect shells, swim in our pristine waters, or just lounge in the sunshine. Whatever your pleasure, you’re sure to find it at Gray Pearl on Chincoteague Island!brbrGray Pearl - Time wasted at the Beach is well spent.....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.

Bed

Bath

Sleeps

$189.89

/ Nightly

Condo

Bliss on the Bay by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Welcome to Bliss on the Bay - leave your troubles at the door, you won't be needing them here! This super charming 1 Bedroom/1 Bath Condo will make you feel a million miles away from the real world. Located on Marsh Island, you'll have amazing Views of both Black Narrows Channel and the Chincoteague Channel. Perfect for a Romantic Getaway or a small Family, you'll have all the makings of a fabulous Chincoteague Island Vacation Experience!brbrAs you take the exit for Marsh Island from the Causeway, you'll feel like you're pulling onto your own private island. With only a handful of homes here, you'll love the peace and quiet. All the festivities of Chincoteague Island are mere steps away, but you return to the sweet serenity that only Marsh Island offers. This tiny Island was formerly a Harbor for Commercial Fishermen that was converted to Waterfront Homes. An adorable Efficiency Condo that has had many updates, you will experience Views that are simply stunning - 360 degrees of Waterfront Views of the Chincoteague Channel, Historic Main Street, the Bay, Marsh, and of course THE most incredible Sunsets to be found. brbrThe Living Area, which directly faces the water, is adorned in shades of Sea Glass, and has a comfy Full Sleeper Sofa and Sitting Area. You'll love relaxing with your morning coffee here, while watching the Herons and Egrets fish for their morning meal. If you're really lucky, you'll get to watch some of our Local Watermen harvesting Oysters - one of our favorite sights in the world. The Kitchenette is adjacent to the Living Area, and has been completely updated with gorgeous Tile Backsplash, Solid Surface Countertops, and Custom Tile Flooring. Well-stocked with all you need, there is a Refrigerator with Freezer, Microwave/Convection Oven, 1 Burner Cooktop, Griddle, Coffee Pot, and more. The Kitchenette is a great place to grab a quick bite before a fun-filled day at the Beach or searching for our Famous Wild Ponies on Assateague. brbrThe spacious Sleeping Area has a comfy Full Bed you'll love sinking into at the end of the day. Tastefully updated and decorated with a Coastal Flair, there is also a Flat Screen TV for Streaming only. The very well laid out Full Bath has 2 rooms - a Vanity Area with Solid Surface countertops, and lots of Storage Space, which leads into the Bathroom with Tub/Shower Combo. In the downstairs Utility Room, there is a shared, free Laundry Facility for your use.brbrLet's get to what you are really here for - the great Eastern Shore Outdoors! Bliss on the Bay offers a wonderful Waterfront Dock. Fish and Crab, right in your backyard. The waters surrounding Bliss on the Bay are shallow and calm - and there is so much to explore, from Oyster Beds to Flounder Fishing! There is also a phenomenal Sun Deck for catching some rays - or enjoy some of our Local Crabs at the Picnic Table overlooking the water, taking in the breezes that Marsh Island is known for. brbrBliss on the Bay - An Ocean Breeze puts the mind at ease.....brbrNo Smoking/No Pets -Seaside 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

Bath

Sleeps

$423

/ Nightly

Private Vacation Home

Pony Swim Crossing by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Pony Swim Crossing - Chincoteague Island is calling…..brbr“To sit in silence at the shore, watch the waves and hear the surf, is to appreciate the very breath and heartbeat of the earth.” ~ UnknownbrbrIsn’t it time to break away from the daily grind The stress, the traffic, and oh, “schedules” - aren’t we all just a little too “scheduled” in life Grab those who matter most, pack a bag, and head on down to our little slice of heaven. brbrPony Swim Crossing sits perched on the Assateague Channel with captivating Views of the Channel and Assateague Island. Tucked away on the ever-popular East Side on Pony Swim Lane, you are literally overlooking where our famous Saltwater Cowboys swim our Wild Ponies over during our Annual Pony Swim. There’s truly no better backdrop to your next Island Adventure. brbrThis adorable Townhome is part of our Flex Stay Program, so no worries if you can’t get away for a full week! Arrive when you want, depart when you want - it’s YOUR Vacation, after all! Beautifully decorated and furnished with a warm Coastal Flair, Pony Swim Crossing is so welcoming, and is perfect for a small family or a few couples to share. As soon as you walk through that door, the wonderful Water Views are center stage - kick off your flip flops and let the fun begin!brbrYou’ll love kicking back in the Living Area after a fun-filled day on the water, and enjoying Free WiFi and Flat Screen TV. Dressed in Coastal Blues and Grays, its palette is pulled from Nature itself. Sink into the comfy Sectional after a fun-filled day at the Beach, or step outside onto the Covered Deck to take in Channel Views that will leave you breathless. Overlooking Assateague Island and Assateague Light, the beauty is hard to describe - you may even see ponies grazing across the Channel in the Marsh. brbrMealtime will feel like a bay breeze in the well-stocked Kitchen! Dine in the comfort of Central AC, or on your Waterfront Balcony, Al-Fresco Style. Not one to cook on Vacation Stroll or take a short ride to many nearby Dining options. The world is your oyster here on Chincoteague Island, after all!brbrPony Swim Crossing sleeps 5 with 2 Bedrooms and a Bonus Room just off of Bedroom 2. Upstairs, Bedroom 1 has a comfy Queen Bed, Flat Screen TV, and a Sleeper Chair perfect for a little one. Down the Hall, Bedroom 2 has another Queen Bed and a Flat Screen TV. Lining the back of the house and just off of Bedroom 2, you’ll find a Bonus Room with a Twin Bed. The door that separates the Bonus Room from Bedroom 2 is a glass sliding door, which would also make this a great family suite! A Full Bath with Tub/Shower Combo is shared, and there’s also a convenient Half Bath downstairs. brbrSo, the Views are great, the home just perfect - what awaits you outside this adorable home A fabulous Pier that extends all the way to the Assateague Channel and a Private Boat Slip that is also a great spot to fish, crab, and launch your kayaks! The Pier to the right belongs to the Chincoteague Fire Department, and is private. brbrFlex Stay, Bayfront, jaw-dropping Bay Views, AND a Private Pier What are you waiting for! Breakaway today - the only trip you regret is the one you don’t take. 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.

2

Bed

1

Bath

5

Sleeps

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