358,603 properties available

Located in Chincoteague Island, Virginia, United States. East Side Breezes on Chincoteague Island - Stupendous Views! Sky above, Sand below, Peace within….. Here at Seaside, we believe that finding the “perfect” Vacation Home is so much more than merely finding a place to lay your head at night. We are all about “Experiences” ~ and a stay at ‘East Side Breezes’ is just that ~ a blissful Experience that will be treasured by your family for years to come. This spectacular Family Home sits on the ever-popular East Side of our beautiful Little Island by the Sea, and faces the Assateague Channel and Assateague Light - and y’all, those Views! East Side Breezes is unique in so many wonderful ways - you’ll feel this as soon as you pull into the driveway!As you climb the few stairs leading to the Waterfront Deck, that salty, sweet sea breeze hits your face, welcoming you to paradise. You can already see yourself never wanting to leave the comfy Adirondack Chairs that face the Channel. Upon entering, East Side Breezes welcomes you like an old friend.

Located in Chincoteague Island, Virginia, United States. Precious Time on Chincoteague Island! There is only one thing more precious than our time, and that is who we spend it on….Life is short - we live in a world where we’re always rushing - even when there’s no rush! We have to force ourselves to slow down - to stop and smell the flowers - or even better, Mother Ocean! If you’ve been longing to get away with those who matter most, we have the perfect place for you…..Welcome to Precious Time on Chincoteague Island - or as we like to call it, “Our Little Island by the Sea”. Precious Time sits in the very heart of our Island, close to everywhere you want to be, but it feels a million miles away from the real world. It’s such a great location - you can take a short stroll down Cropper Street to watch the sunset over the Chincoteague Bay, or wander to Historic Downtown Main Street’s Shops, Restaurants, and the Waterfront Park, home of many free events during the Summer season. Assateague National Seashore, where our famous Wild Ponies roam fre

Located in Chincoteague Island, Virginia, United States. Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague Family Tides - The tans may fade, but the memories last forever! Looking for somewhere truly special to spend your Chincoteague Island Family Vacation this year? Look no further, as special doesn't even begin to describe the tranquility and beauty of waterfront Family Tides. This adorable home is located directly on Lewis Creek's deep water, so by all means, bring the boat, kayaks, jet skis, or water toy of choice! With sweeping views of the Marsh, Canal, and Chincoteague Bay, you will feel as if you have found paradise. Family Tides has all of the touches and charm of a historic island home that you love, plus the modern amenities you need. Located in a fabulous location on Main Street, you can walk or ride your bike almost everywhere you want to be. This adorable 3 Bedroom/1.5 Bath home comfortably sleeps 8, with more than enough room both inside and out to enjoy time together. As you pull into the dri

Located in Chincoteague Island, Virginia, United States. The Rose Cottage - Adorable and Affordable. Just give me the Sea and a little Cottage to be…..Looking for the perfect Island getaway for your family? Welcome to The Rose Cottage - adorable and affordable in the heart of Chincoteague Island. Located in a peaceful, quiet part of our wonderful Island, you'll enjoy the serenity here after a busy day of exploring Assateague Island. Close to everywhere you want to be, with the feeling of being a million miles away.....The Rose Cottage is a shabby chic lover’s paradise, with colors of sea glass and shoreline - a palette pulled from Nature itself. Kick back in the comfy Living Area with Free WiFi and Flat Screen Smart TV. Filled with wonderful natural light from huge bay windows, it’s such a refreshing space. We’re so in love with the Rustic Hardwood Floors, reminiscent of a stroll on the Boardwalk. It’s the perfect place to relax after searching for Wild Ponies!Just off the Living Area, you’ll find the well-stocked Kitchen with Stainless Appl

Located in Chincoteague, Virginia, United States. 1BR Snug Harbor Waterfront cottage with a lighthouse view! It is a unique and cozy waterfront cottage with the most amazing view of the National Park, the wildlife Refuge, the lighthouse and the spot where the wild Chincoteague ponies hang out! This cottage is a part of 10 cottages complex. It is a quiet, relaxing location and only 5-10 minutes drive to the town or the beach.

Located in Chincoteague Island, Virginia, United States. No Problem (Formerly The Teague House) - Wonderful Waterfront! Life is good, but Island Life is better!Looking for a Beach Break that will take your breath away, yet not break the bank? Welcome to No Problem on peaceful and serene Marsh Island! This Newly Renovated Townhome in Captain’s Quarters Townhomes has it all, and is just a stone’s throw from our beautiful Little Island by the Sea!As 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 that Marsh Island offers. 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. At No Problem, take in Bay Views that are simply stunning - Water Views of the Chincoteague Channel, Historic Main Street, the Bay, Marsh, and of course THE most

Located in Chincoteague Island, Virginia, United States. Lily Pad 2 - Brand New and Dog Friendly! “Not all who wander are lost…..”Welcome 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!Brand 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!You’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…..You’ll love kicking back in t

Located in Chincoteague, Virginia, United States. George's Retreat - Tucked away, yet close to the Beach! Traveling - it leaves you speechless, then turns you into a Storyteller. Welcome to the Chincoteague Island Retreat you've been longing for - tucked away on a quiet lane in the heart of our tiny Island. George's Retreat is in the perfect location, just off of Maddox Boulevard, aka the Beach Road - you can walk or ride your bike to many, Restaurants, Shops, and Activities up and down the Boulevard, and the Beach is a short bike ride away. This delightful Duplex sleeps 6 with all the comforts of home and then some. And driving down the sleepy dirt road to the Cottage, you will know right away you won't be disturbed by the hustle and bustle of the busy season. George's Retreat is just perfect for a family or even several couples traveling together. As you enter, you'll love the modern Coastal Decor, welcoming colors of Sand and Sea, and comfortable furnishings. The Living Area has plenty of room for all, and is a great place to relax

Located in Chincoteague, Virginia, United States. The Oaks - 2BR Island home close to town & shopping. Linens provided! Very bright & nice 2/3 bedroom cottage with convenient in town location. Enjoy your morning coffee on the front sun porch or walk to town for breakfast and visit the shops. This island home is a delight. Beloved traditional island home with a steep staircase and most bedrooms are on the 2nd floor and small bedroom off kitchen with accommodate teens or kids. This house has window a/c .Linens and Towels Provided. Even a Pack-N-Play for a little one. ( No Washer and Dryer) Please ask about our cancelation policy. 60 day cancellation prior to occupancy date (100% refund minus processing fee, travel insurance and credit card fee's). This Property has a 3 Night Minimum*** Bed Sizes: 2Q, 1T, Da

Located in Chincoteague, Virginia, United States. Chincoteague Island Cottage ~ 2 Mi to Beaches Calling all beachgoers for Chincoteague Island fun! This cozy beach cottage is the ideal abode for your next East Coast adventure. Enjoy days with your toes in the sand and a cold beverage in hand on Chincoteague Beach. Charter a fishing boat and cast a line for the catch of the day or take in the sights of the island from one of the local tours. You also won't want to miss the fresh seafood at the local eateries, just a hop, skip, and a jump from your front door. Chincoteague adventures await!-- THE PROPERTY --Free WiFi | Proximity to Beach | In-Unit LaundryThis cozy beach cottage is ready to welcome small families or groups for adventures on Chincoteague Island.Bedroom 1: King Bed | Bedroom 2: Queen Bed, Twin DaybedKITCHEN: Fully equipped, Keurig coffee maker, dishware & flatware, spices, under-counter fridge, gas rangeOUTDOOR LIVING: Front porch, lounge seating, yard space INDOOR LIVING: Smart TV, dining table, hardwood flooring, beach d

Located in Chincoteague, Virginia, United States. Waterfront Unit on Assateague Channel View with Floating Dock Waterfront on the Assateague Channel! The Sea Tag Lodge is loved by all for the views, dock, and ideal location. Perfect for kayakers, bikers, bird watchers, and those that like to play on the nearby playground!2-bedroom, 1 bath condo with a dedicated boat slip on a large, private floating dock on the Assateague Channel across from the Lighthouse.Bedroom 1:  Queen bed and flat screen tvBedroom 2:  Twin over Full bunkbed and a flat screen tv for DVDs viewing only.  Closet includes a Pack-n-Play crib. Living Area:  Wifi, Direct TVLocated 200 yards from Memorial Park and playground, launch your boat and pull up to the dock in minutes.  Watch the sunrise as ponies graze on the banks of Assateague.  Enjoy your morning coffee on the back deck or your dinner of fresh crabs caught off the dock at the picnic table just outside your back door.  Common grounds have 4 charcoal grills for your use as well as a laundry room with coin op

Located in Chincoteague, Virginia, United States. Pony Swim - Water Front Duplex with beautiful views. Top & bottom View decks Amenities: Central A/C, Dish TV, VCR, Microwave, Dishwasher, Keurig, W/D, WiFi, DecksWaterfront duplex located on East Side Drive. This beautiful property has a with great views of Assateague Island and the Lighthouse. Newly remodeled kitchen, living room, and dining room. Kitchen is open to the dining room, perfect for entertaining while you cook! Currently Dock is being repaired. You cannot dock a boat at this time. Great views and Memorial Park just around the corner to fish and crab. Please ask about our cancelation policy. 60 day cancellation prior to occupancy date (100% refund minus processing fee, travel insurance and credit card fee's). Bed Sizes: 1 Queen, 4 TwinsSaturday Change Over$ 193-270 Nightly plus tax & fees**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Located in Chincoteague, Virginia, United States. Sunset Bay Villas at Chincoteague Island Virginia - direct water front Sunset Bay Villas on Chincoteague Island Welcomes Bird Watchers, Nature and Beach Lovers! Designer condo that is on the shore of Chincoteague Bay with direct views of the Intracoastal Waterway, Chincoteague Channel, Chincoteague Bridge, Wallops Flight Facility, Wallops Island and Marsh Island . From this unit you will enjoy sunrises, magnificent sunsets, waterfowl, dolphins, bald eagle which are all part of the natural beauty on Chincoteague Island. The designer kitchen has beautiful bronze fixtures with upgraded cabinetry, tile back splash, gorgeous appliances plus lighting on dimmers to set the mood - Antique Mahogany Duncan Phyfe Dining Table with leaf for expansion to seat 8 for family dining - enjoy water view dining with large nine foot window by table. In the Master Bedroom there is a nine foot window overlooking the water plus large slider onto the deck, oversized windows overlooking the water in both second

Located in Chincoteague Island, Virginia, United States. Charlie's Cove - Pet friendly w/ Fenced yard! Charlie's Cove is waiting to accommodate you and your guests! Conveniently located on Ridge Road in the middle of Chincoteague Island, you will find yourself immersed in complete comfort. Upon stepping through the door you are greeted by the simple, yet welcoming décor. An oversized couch is sure to relax you after a long day in the sand, cuddle up and watch a movie or play a board game! Charlie's Cove has it all... The kitchen is perfectly designed, offering an abundance of place for the cook in your family to prepare meals. There is a private den if you'd like to spend some quiet time away from the group. This home offers 3 large bedrooms - the primary features a Queen bed and en suite bathroom with large soaking tub and stand-alone shower. The second bedroom features another Queen bed, while the third bedroom has 2 Twin beds. Bring your furry friend to run in the fenced in yard - Charlie's Cove is pet friendly! **While this home will ac

Located in Chincoteague, Virginia, United States. Mae's Landing - Comfortable 2BR home close to Memorial Park & boat launch Amenities: Window A/C, Keurig, W/D, 2 Smart TVs (Bring your own login for streaming apps), DVD & VHS Players, WiFi, Charcoal Grill, Deck, Back YardVery nice two bedroom home, tucked away for a quite getaway with views of the channel. Nice size back yard with deck. Within walking distance to Memorial Park and boat launch.. Please ask about our cancelation policy. Parking for 2 cars only. 60 day cancellation prior to occupancy date (100% refund minus processing fee, travel insurance and credit card fee's). Pet friendly home. $75. (Per pet) will be added to your reservation. ** Limit 2 cars only ***This Property accepts Small and Medium Dogs Only***Bed Sizes: 1 Queen, 2 Twins, 1 Queen Sleep SofaSunday Change Over$ 90- 185 Nightly plus tax & fees**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Located in Greenbackville, Virginia, United States. Salty Sea Lyons Landing - Pet friendly! Escape to the ocean and enjoy this contemporary golf course home! Sit and relax while enjoying the golf course views from the screened porch; boasting easy access to pools, golf course, restaurant, and much more. Come relax in the cozy living room with new furnishings, electric fireplace and smart tv. The well-equipped kitchen boasts stainless steel appliances and kitchen equipment that guests can use to cook tasty snacks.The home includes four smart TVs, (one in each bedroom) central heat and a/c, and plenty of board games to keep you occupied during your stay. Bedrooms are equipped with nice mattresses to ensure a good night's rest, along with cozy blankets and thoughtful décor. The owner's suite features a king sized bed, electric fireplace, on suite bath with a double vanity, large jacuzzi tub as well as a walk in shower. You will find two more bedrooms just down the hall, one with a queen sized bed and another with a double bed. There

Located in Chincoteague Island, Virginia, United States. One Particular Harbor on Chincoteague Island! Changes in Latitude, Changes in Attitude…..As Jimmy Buffet would say, welcome to One Particular Harbor! And just as his music has a way of relaxing and rejuvenating us, so does this fabulous Vacation Home in the heart of Chincoteague Island. This absolutely adorable Cottage is not only Pet Friendly (see restrictions below), it’s in an awesome location on Ocean Boulevard. Walk or ride your bike to many Shops, Restaurants, the Beach, and The Island Creamery - if you’ve been here, you know this is a must - and it simply oozes that quintessential Chincoteague Charm! As you pull up to the house, you can already envision yourself sipping Sweet Tea on the cozy Front Porch as folks stroll by enjoying our little Island by the Sea. Warm and welcoming, One Particular Harbor has all the makings to be your Chincoteague Island vacation destination. You’ll be welcomed by stunning Hardwood Floors, and muted Earth Tones with pops of Aquas and Blues. You’ll

Located in Chincoteague Island, Virginia, United States. Dragonfly Point - Waterfront home w boat dock & deck! "DRAGONFLY POINT" is a magnificent waterfront property on Oyster Bay & canal. Surrounded by water on three sides of the home, you see the bay and canals from every window! The abundance of decking for entertaining will amaze you with easy access on both floors. Upper family room/loft with unobstructed views.The home has beachy-chic feel with built in bookcases, shiplap, custom fixtures and bathrooms, and more. Two master bedroom suites - upper and lower. Totally fenced in yard that has mature plantings, kayak launch with concrete pad, 120' pier that extends into the bay, comfortable screened porch and much more! Many updates recently including washer & dryer, brand new kitchen & appliances, new bathrooms, etc. SIMPLY BREATH TAKING VIEWS! Come for a stay at Dragonfly Point - it's one you surely will not forget! - This property has a 7 night minimum stay year 'round. ​​​​​​​- No smoking is permitted on the premises. - Linens and towel

Located in Chincoteague Island, Virginia, United States. Whelks on Willow - Private Pool! Whelks on Willow - Live in the Sunshine, Swim the Sea, drink the Wild Air..... Welcome to Whelks on Willow - a lovely Coastal Cape Cod tucked away on Willow Street - close to everywhere you want to be, yet a million miles away from the worries of the real world. Featuring a refreshing Private Pool, Whelks on Willow is truly a Vacation Destination that sleeps 8 in comfort and style. You'll love relaxing in the Living Area with Free WiFi and Flat Screen TV after a fun-filled day at the Beach, which is only about 7 minutes away. With lots of oversized, comfortable furnishings, it truly has that home away from home feel. There's even a cozy Fireplace for those chilly Off-Season Stays - one of our favorite times on our little Island by the Sea!The Chef in your family will love the well-equipped Kitchen - mealtime will be anything but a chore! Well-stocked with all you need, there's no need to dine outevery day, unless you want to, that is! You can dine indoo

Located in Chincoteague Island, Virginia, United States. The Pearl at Grand Bay on Chincoteague Island! Salty air breezes and the sweet serenity of pond-front living await you at The Pearl at Grand Bay. This Newly Remodeled End Unit Townhome has it all - magnificent Water Views, and a stunning interior. Located on the ever-popular East Side, you can have the Chincoteague Vacation you’ve been dreaming of at a very family-friendly price tag - and even your family dog can enjoy this Vacation!If you’re not familiar with the East Side, imagine driving down a quiet road that hugs the shoreline of the Chincoteague Channel - glancing out over the water, you will see only Assateague National Seashore and our famous Lighthouse - you may even see some ponies grazing in the marsh across the water! Grand Bay Court is in just the perfect location - you can easily stroll to Memorial Park to enjoy the Playground, Kayak and Boat Launch, Crabbing, Fishing, and more, and are just a short stroll from waterside dining at Etta’s Restaurant. As you pull up to The

Located in Chincoteague Island, Virginia, United States. Sunset Bay Villas - 'Sunset in Paradise' * Amazing Water Views & Sunsets ANOTHER DAY IN PARADISE CHINCOTEAGUE *** One of the Top Guest Rated Properties on the Island ***Owner Operated by: Annie SwitzerUnit 213 has 3 bedrooms, 2 baths, hardwood floors, granite counter tops, beautiful decor, and amazing water views!This second floor condo was new to the rental market for 2013 and is located close to the fitness center and swimming pool. It is beautifully decorated in a coastal theme. There are many custom upgrades such as cherry wood floors, granite counter tops, and Jenn Air appliances. It is the only unit in Sunset Bay with an extra large shower with multiple jets in the Master Bath. It also has an open lay-out and all of the amenities in Unit 103 (our first condo at Sunset Bay - VRBO #304765) including a gel fuel fireplace. There is a custom shower instead of a jetted tub in the Master Bath.Beautiful second floor condo in Sunset Bay is located has a breathtaking sunset view over

Located in Greenbackville, Virginia, United States. Shellfish Time in Captain's Cove! Relax, Rejuvenate, and Reconnect…..Welcome to Brand New ‘Shellfish Time’ on the beautiful Eastern Shore of Virginia! If you have been looking for a “different” kind of Vacation - a totally new Experience, yet not too far from Home, boy, do we have the place for you! Get ready for an awesome Adventure at this fabulous Brand New Home - the Beach, Wild Ponies, incredible Amenities - the only thing missing is YOU!Captain’s Cove is one of the Best Kept Secrets on the Eastern Shore of Virginia! Located only 25 short minutes by car or boat to Chincoteague and Assateague National Seashore, where our famous Wild Ponies roam free, you will never run out of things to do. And have y’all heard about our Oysters (pronounced Arsters here on the shore)? They are second to none. If you’re looking for some OC excitement, Ocean City, Maryland is a short 45 minute drive away. Have the very best of everything, right in the heart of the Eastern Shore! But once you see this

Located in Chincoteague Island, Virginia, United States. Safe Harbor on Chincoteague Island! Welcome to Safe Harbor on magical Chincoteague Island - the perfect place to relax, rewind, and reconnect. This adorable Dog-Friendly ($100 per dog) Cottage simply oozes that quintessential Chincoteague Charm you love so much, while giving you the Modern Amenities you need. Located in the heart of our Island at the corner of Chicken City and Ridge, you’re close to everywhere you want to be, yet will feel so far away from the stresses of daily life - you’re on Island Time now!Safe Harbor feels like just that - a relaxing getaway - a place to let your troubles be forgotten. As you pull into the driveway, you’ll love the Beachy Style of Safe Harbor - Tropical Colors, inviting Landscaping, and a Patio that you cannot wait to sip Sweet Tea on. Fido is already scopint out the Brand New Fenced Yard - just perfect for a game of fetch! Kick off your Flip Flops in the Mud Room, and the good times begin…..You’ll love taking a breather in the Living Area with Fl

Located in Chincoteague Island, Virginia, United States. Touch of Grey- Waterfront, Pet Friendly Welcome to "Touch of Grey," a delightful waterfront rental that blends comfort, style, and convenience into a perfect living space suitable for a variety of lifestyles. This well-appointed house includes three bedrooms, two bathrooms, and a range of updated amenities that ensure a seamless living experience.Inside, discover a thoughtful layout featuring smart TVs throughout, high-speed WiFi, and a mix of privacy and social spaces that cater to both relaxation and entertainment. The screened porch offers a serene retreat, perfect for enjoying the outdoor air without the bother of pests, and the open deck invites you to bask in the stunning views that surround you.Step outside to explore the outdoor space that this property generously offers. A large deck overlooks the tranquil waters, ideal for peaceful mornings or lively evening gatherings. The highlights of the outdoor area include a personal boat dock, which provides immediate water access for