Vacation Home Rentals By Owner In Chincoteague Island, VA

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.

Pony Swim Crossing by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

1

Bath

5

Sleeps

$350.87

Welcome to Island Bay Dreams in the very heart of Chincoteague Island! This absolutely adorable 4 Bedroom Townhome truly has it all, and is less than 10 minutes away from Assateague National Seashore, where our famous Wild Ponies roam free!brbrYou know when you walk into a home and instantly feel your worries vanish That’s exactly the vibe we get from Island Bay Dreams! Decorated with tasteful beach decor, soothing coastal colors, and comfy furnishings, it screams “you’re on island time now”! Which after driving a few hours to get away from the realities of everyday life, is just what you need….brbrPinewood is a small grouping of only 4 Townhomes tucked on Deep Hole Road - close to everywhere you want to be, yet you’ll still feel a million miles from the real world. As you enter through the Kitchen, you can see they’ve made such great use of the space. The Eat-in Kitchen has beachy white cabinetry, and bar seating that spans the length of it. With all the comforts of home, mealtime will be easy breezy. If you’re not one to cook on Vacation, you’re only a short stroll from some great dining options, including Captain Zack’s - and trying their Bloody Mary with oysters, crab, and shrimp is an absolute must! brbrYou’ll love grilling some cheeseburgers in paradise on the Charcoal Grill out back, and sinking into the Adirondacks and enjoying the Fire Pit. What a great place to end each day, and share stories of the day’s adventures!brbrWandering down just a couple of steps to the Living Area, you’ll find a wonderfully warm and comfortable space with wood walls, beachy flooring, and comfy leather-like sofas to sink into after a fun-filled day at the Beach. There’s room for all here with multiple seating areas and even a Pub Table. Enjoy Free WiFi and Smart TV for a fun family movie night, or just hand out and be together - something that can be hard to find time to do in today’s busy world. brbrIsland Bay Dreams sleeps 12 in 4 Bedrooms, and is perfect for one large family, or for 2 smaller families to share, which definitely helps cut costs! Bedroom 1 is on the 1st Floor just off the Living Area, and has a comfy Queen Bed, Smart TV, and Attached Full Bath with Tub/Shower Combo. The Full Size Washer and Dryer is also housed in this Bathroom. Dressed in colors of sand and sea, it’s sure to be a restful retreat, and perfect for those who don’t want to contend with stairs. brbrWandering upstairs, you’ll find 3 more Bedrooms and another Full Bath with Tub/Shower Combo. Bedroom 2 also has a Queen Bed, Smart TV, and beachy decor. The kiddos in your group will adore Bedroom 3, which has 2 Twin Beds and a Pyramid Bunkbed, and can sleep up to 5, along with a Smart TV. Finally, huge Bedroom 4 has a Queen Bed, Smart TV, and a Twin Bed - a perfect family suite for parents who may want to keep a child nearby. brbrAll of this, and you’re just a hop, skip, and jump away from one of the most pristine and visited beaches in America! Whether you’re searching for Wild Ponies, fishing, shelling, surfing, or just sunbathing, our beautiful beaches have something for everyone! There are also 3 kayaks you're welcome to use, as well as a variety of boogie boards and beach toys! Island Bay Dreams is proof that you can have it all without breaking the bank!brbrNo Smoking and No Pets - Owners have a dog. Owners have Exterior Security Cameras. 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.

Island Bay Dreams by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$369.66

This charming rancher is ready to welcome you and your family. Come make memories in the cozy and relaxing space. Enjoy this redone home on large lot perfect for family games of kickball and tag after a fun day at the beach. This home sleeps 8-9 folks comfortably. It has a stocked kitchen, a dining area and living room with 4 bedrooms and 2 full bathrooms. There is an outdoor shower and foot rinse (April-November). Just added for Fall 2024: Disc Golf unit for the backyard and 8 new outdoor chairs. brThe driveway can hold roughly 8 vehicles, please do not park (or drive) on the grass. This home is walking distance to the Veterans Park (.8 mile) and is away from the town's bustle. We are a 7 minute drive to the beach and roughly a 20 minute bike to the beach. The Brass Crab is set up with families in mind with child friendly spaces, bunk beds and open places to play, but can easily work for 3 couples as well.brQueen rooms are on the East side of the house, the other two bedrooms are on the west. The main living space is in the middle of the 4 bedrooms. All rooms have white noise makers and blackout curtains.brAll rooms have space for a pack-n-play. A pack-n-play, portable highchair, and a diaper changing pad are available in the bunk closet. This closet also contains outdoor games and the rainy day box. We will leave these in place but recommend you clean them prior to your use. brThere is 1 TV in the living room and wireless internet. We provide Prime video and Netflix.brThis is a 3/4 acre lot with a large front yard and a fenced backyard. A walkway, patio, and fire pit area have been added to the outdoor space for additional fun and relaxation! You'll need to bring your own wood, and you'll want bug spray.brPlease send a message with additional questions and we would be happy to help.

The Brass Crab - Check in/out any day!

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$278.12

3BR/2.5B***(1BR+1.5B down/2BR+1B up) {2Q, 2T} Amenities: Central A/C, Microwave, Dishwasher, W/D, Smart TV, Gas Grill, Screen Porch, Deck, WiFi, Fireplace, Garage, Community PoolbrbrAmenities: Central A/C, Microwave, Dishwasher, W/D, Cable, Smart TV, Gas Grill, Screen Porch, Deck, WiFi, Fireplace, Garage, Community PoolbrbrBeautiful spacious duplex with a screened porch and a Community pool. Offers wireless internet, Smart TV. Close to carnival grounds!brbr NO LINENS AND TOWELS PROVIDED SO BRING YOUR OWN OR CALL US TO REMT THEMbrbrCancellations 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: 2 Queens, 2 TwinsbrbrSaturday Change Overbrbr2026 Prime Season Rates $ 1645 per week - 7 night minimumbr2026 Off Season Rates $ 1155 per week / $ 165 per night with 3-night minimumbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Island Pony - Outstanding 3 BR W/F Duplex/community pool NO LINENS

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$432.18

Discover your own piece of paradise at this incredible beach getaway! 'Our Happy Place' is the perfect retreat for up to 7 guests seeking comfortable, tastefully decorated accommodations. This cozy vacation home is clean, simple, and fully furnished, including amenities that will make you feel right at home. Even your furry, 4-legged family members can join in on the fun, small to medium dogs are welcome.brbrSituated in the desirable Oyster Bay I waterfront community, 'Our Happy Place' is located at the end of a wide-mouth canal, offering unobstructed water views and a private dock platform. You'll love the convenience of being situated next to the community boat ramp, making it easy to launch your watercraft for a day of adventure.brbrRelax and unwind on the expansive wrap-around screened porch overlooking the water, featuring plenty of comfortable seating and a dining area. Savor your morning coffee or sip a cool drink after a day at the beach.brbr'Our Happy Place' is a single-level home with 3 cozy bedrooms that can accommodate up to 7 guests. The bedrooms include 1 queen, 2 twins, and 1 bunk bed (twin over double). There are 2 full bathrooms, one of which is a tub shower combo.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.

Our Happy Place | Canal Front w/ Private Dock, Huge Screened Porch + Pet Friendly Escape

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$332.01

Sunny Shack - The Best Days are Beach Days..…..brbrWelcome to Sunny Shack on wild and wonderful Chincoteague Island! This stunning Waterfront Dream Home has been a fan-favorite Vacation Rental for years!brbrAhhhh, South Main Street - if you aren’t familiar, South Main is home to some of THE most amazing Sunsets to be had on our little Island by the Sea. Add that to Sunny Shack’s incredible list of Amenities, and you have the makings of a perfect Chincoteague Island Vacation! This incredible home sleeps 10 in 3 Bedrooms, and is loaded with every bell and whistle - even a Game Room with Pool Table and Ping Pong, and even a Monopoly Table!brbrEntering Sunny Shack on the ground floor, you can kick off your flip flops in the spacious foyer, greet the cutest Chincoteague Pony allowed to live indoors, and let the fun begin! You can’t help but check out the Game Room, also on this level. You’ll find both Pool and Ping Pong Tables, and a Roku Smart TV in a cozy Sitting Area.brbrWandering upstairs, you’ll be captivated by Colors reminiscent of the Sea - and those Views! Sunny Shack has had every upgrade imaginable - from Custom Hardwood Floors to Flat Screen 3D Smart TV! You’ll love relaxing in the oversized, comfy Living Room furniture with breathtaking Bay Views right from the sofa. Sunny Shack’s open layout is just perfect for spending time with those who matter most, without ever feeling crowded. The spacious Living Area opens to the well-equipped Kitchen, which the Chef in your family is sure to fall in love with. With Gleaming Granite and Stainless Steel Appliances, mealtime certainly won’t feel like a chore. You can dine indoors in the comfort of the AC, or Al-Fresco on the Bayfront Deck. If you want to be really creative, pack a picnic and enjoy lunch on the Shared Pier, which even has a picnic table!brbrAround the bend, you’ll find yet another Living Area - bright and beachy in Nautical blues and whites, it’s a great place to curl up with a good book. brbrThe Waterfront Master Bedroom, located on the other side of Sunny Shack has a comfy King Bed! Slip out to your Private Waterfront Balcony to stargaze while everyone else slumbers - just take in that salty, sweet sea breeze. The Master has a 65 inch Roku Smart TV, as well. The Master Bath has both a Tub/Shower Combo, a Walk-in Shower, and Double Vanity. brbrBedrooms 2 and 3 are distanced from the Master, allowing lots of privacy. Bedroom 2 sleeps 6 in 2 Pyramid Buns (Twin over Full) - there’s also a 3D Smart TV here! And finally Bedroom 3 is adorned in beachy blues with a Queen Bed and Smart TV.brbrSunny Shack is so much more than a place to lay your head at night - the Outdoor Living is beyond fabulous, as well! The Pier is shared with only 2 other homes, and perfect for fishing, crabbing, launching kayaks (2 kayaks are provided for your use!), or simply just taking a nap in the Hammock on the pier. There’s so much to do, but chilling to some Jimmy Buffet while watching the boats go by is a must, as well - take it from us, you Chincoteague Vacation Experts!brbrSunny Shack - Sky above, Sand below, Peace within….brbrbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. We do NOT rent to party groups, high school groups, or bachelor-type parties.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.

Sunny Shack by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$261.95

Sugar Shores - Your next Vacation can be both Salty and Sweet!brbrWhen was the last time you had a Vacation that took your breath away It’s the perfect combination of the right Destination, the right Vacation Home, and the perfect Location. Sugar Shores on beautiful Chincoteague Island is all of that and more, and only a few minutes from Assateague National Seashore, where our famous Wild Ponies roam free. If you’ve been looking for the ONE, this is it. What makes it even sweeter You can bring your well-trained dog - up to 2 - with a $100 Pet Fee each!brbrSugar Shores is not just a place to lay your head at night - it’s a true Home away from Home, with all the comforts and peace that come along with that. Tucked in a quiet location on Ridge Road, you’ll enjoy those salty, sweet breezes from 2 Levels of Covered Decks facing the Chincoteague Channel with Partial Channel Views. brbrYou’ll love relaxing in the comfortably furnished Living Area with Free WiFi and Flat Screen Cable and Streaming TV after a fun-filled day at the Beach. Sink into the Sectional and kick back surrounded by Colors of Sand and Sea. The fabulous Flooring is reminiscent of a stroll on a beachy boardwalk, and we just love the tasteful Coastal Decor with touches of our history rooted in our Wild Ponies we’re so known for. brbrThe Chef in your family will adore the Well-Stocked Kitchen with its Vibrant Blue Backsplash and ample Countertop Space. Mealtime will be a bay breeze, and you can dine in the comfort of Central AC in the Dining Area, or enjoy a bite on the Front Porch. Grill the Fresh Catch of the Day, which hopefully you caught, on the Gas Grill in the Fenced Backyard. Not one to cook on Vacation We’ve got you covered! There are so many great Dining options just a few minutes away! Also on this level you’ll find a Full Bath with Tub/Shower Combo. brbrSugar Shores sleeps 6 more than comfortably. Wandering upstairs, you’ll find 3 beautiful Bedrooms and another Full Bath. Bedroom 1 is a Master Bedroom facing the Chincoteague Channel. With Private Access to the upper Covered Deck, you can slip out to stargaze while everyone else slumbers. What a great place to begin and end every sweet, special Vacation Day. You can curl up with a good book on the Outdoor Sofa, sip Sweet Tea in one of the Rockers, or enjoy your morning coffee at the Bistro Set. The Bedroom itself is a peaceful retreat with Crisp Whites and Sea Salt, a luxurious King Bed, and Flat Screen TV. Bedroom 1 has Private Access to the Full Bath with Tub/Shower Combo, which is a Jack and Jill Bath - the other door leading to the Hall. brbrDown the Hall, Bedroom 2 is adorned in relaxing pastels, and has a comfy Queen Bed and Flat Screen TV. Bedroom 3 is perfect for the kiddos with a Pyramid Bunk (Twin over Full), Flat Screen TV, Work Space, and even some Games for your enjoyment!brbrSugar Shores is close to everywhere you want to be, yet nestled in a quiet location away from the hustle and bustle. This perfect family friendly Retreat is ready to help you relax, reconnect, and rejuvenate! brbrSugar Shores - It’s a sweet, sweet Life living by the Salty Sea!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Well Trained Dogs allowed with a $100 Pet Fee - 2 dog max. Dogs must be on flea/tick preventative and up to date on vaccinations. Pet Damage not covered by Accidental Damage Waiver. 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.

Sugar Shores by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$179.68

Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)!brbr4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. Small fishing town on the eastern shore of Virginia. Central air, newly updated and fully equipped kitchen (pots, pans, dishes, seafood equipment, some spices, blender), screened in porch and outside enclosed hot running shower, sleeps 10. Great for 2 families, includes high chair and portacrib. The house is within walking distance of the town. Check out Chincoteague, a real all American town with activities and a pristine protected beach. Flat for great bike riding. And great all year 'round. Beach umbrellas, beach chairs, coolers, barbeque grill, washing machine, dryer and clothesline. Need to bring towels and bed linens. Beach toys provided.

Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!

Chincoteague Island, Virginia, United States

4

Bed

Bath

10

Sleeps

$770.9

**Island Living at Its Finest — Where Sunrises Steal the Show**brbrWelcome to the most breathtaking views Chincoteague Island has to offer. Nestled in the sought-after Oyster Bay I Community, this stunning three-bedroom, three-bathroom rental home is a haven for those who crave inspiration from the natural world. If you're an artist, writer, creator, or simply someone who finds peace in golden-hour magic, this is where you belong.brbrStep inside to discover a thoughtfully designed living space that includes a comfortable living room and an additional den — perfect for curling up with a good book or sketching the marshland views that stretch endlessly beyond your windows. Feeling playful Challenge your guests to a round of bumper pool, because every retreat deserves a touch of friendly competition.brbrThe real magic unfolds across multiple levels. Climb the spiral staircase to the third-level tower room, where panoramic vistas will leave you utterly speechless. Gorgeous sunsets paint the sky in hues you didn't know existed, and you'll find yourself reaching for a camera — or a canvas — night after night.brbrOutdoor living shines here with spacious decks ideal for entertaining and a screened porch complete with a ceiling fan, offering bug-free relaxation while the island breeze does the rest. It's the kind of space where conversations linger and worries disappear.brbrBeyond the home, adventure awaits. Explore the nearby Island Nature Trail for serene walks through coastal landscapes, catch waves at Assateague Beach where wild ponies roam, or bring the family to Maui Jack's Waterpark for splashing fun on warmer days.brbrThis is more than a rental — it's an experience that feeds the soul. Reach out today to secure your island escape and experience these legendary sunrises over the bay.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.

Sunrise View | Waterfront, Kayaks, Gorgeous Sunrises!

Chincoteague Island, Virginia, United States

Bed

Bath

6

Sleeps

$280.2

Check out this clean, modest island duplex home tucked on a quiet side street, just minutes from the action on Maddox Boulevard—close enough for convenience, far enough for peace and quiet (and fewer surprise seagull critiques).brbrInside, you'll find a comfortable 3-bedroom, 1.5-bath layout that's easy to vacation in and even easier to maintain. The primary bedroom offers a restful retreat after beach days and bike rides, while the additional bedrooms flex nicely for guests, a home office, or that hobby you swear you will start this year. Two full bathrooms keep mornings moving, even when everyone suddenly decides they need to leave at the exact same time.brbrStep out to the screened porch for morning coffee, evening breezes, and bug-free lounging—the kind of simple luxury you'll wonder how you ever lived without. The vibe here is relaxed and practical, with a welcoming feel that lets you settle in quickly and start enjoying Chincoteague life right away.brbrWhen it's time to explore, hit the nearby Island Nature Trail, cool off at Maui Jack's Waterpark, grab essentials at Island Foods Great Valu, or make a beach day out of Assateague Beach.brbrReady to claim your slice of island calm Book your vacation today!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.

Half Shell | Clean accommodations close to Beach Road!

Chincoteague Island, Virginia, United States

Bed

1

Bath

8

Sleeps

$389.65

A wonderful canal-front getaway located in the desirable Oyster Bay community.brbrThis home offers effortless access to the water, with the community boat launch just down the street and your own private dock right outside the door—perfect for boating, crabbing, kayaking, or simply relaxing by the canal.brbrThe first floor features a spacious open concept living room, dining area, and fully equipped kitchen, along with a bedroom with a queen bed and a full bath with a shower. A comfortable screened porch and a canalfront balcony provide inviting spaces to enjoy peaceful water views.brbrUpstairs, one bedroom offers a queen bed and its own canal front balcony, while the other includes a full bed and two twin beds—ideal for families or larger groups.brbrLaunch the provided kayaks directly from your backyard, explore the quiet canals, or dock your boat at your private pier. Whether you're seeking adventure on the water or quiet moments by it, this canal-front home delivers the full Oyster Bay experience.

Oyster Catcher- Canalfront with Kayaks & Boat Dock

Chincoteague Island, Virginia, United States

Bed

1

Bath

6

Sleeps

$210.49

Slow down and settle into On Island Time, a thoughtfully updated Waterman’s cottage that captures the true spirit of Chincoteague Island. This inviting two-story home blends timeless coastal charm with modern comforts, creating a warm, relaxed space that instantly feels like vacation.brbrTucked away on a quiet, low-traffic street, this 3-bedroom, 2-bath retreat offers the best of both worlds—peaceful privacy with easy walkable access to local shops, restaurants, and island favorites. It’s the perfect setting for families, couples, or small groups looking to experience Chincoteague like a local.brbrInside, you’ll find a bright, comfortable living space with tasteful updates that preserve the home’s historic character while adding the convenience today’s travelers expect. Cozy bedrooms and flexible gathering spaces make it easy to unwind after a day of exploring.brbrStep outside and discover one of the home’s standout features: a large, private backyard designed for making memories. Fire up the pit for cozy evenings under the stars, enjoy morning coffee in the fresh coastal air, or rinse off sandy toes in the outdoor shower after a beach day.brbrLocated just minutes from the Chincoteague National Wildlife Refuge and Assateague Island beaches, you’ll have easy access to hiking, biking, kayaking, and the famous wild ponies—while still enjoying your own quiet slice of island life.brbrWhether you’re here for adventure or pure relaxation, On Island Time is more than a place to stay—it’s your home away from home on Chincoteague.

On Island Time | 3BR Walk to Town • Fire Pit • Quiet St

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$412.77

Villa 206 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with private luxury bath and private exit to the waterside balcony. Villa 206 will sleep 8, and there are a total of 4 TVs. A laundry room within the unit houses your washer & dryer. Your stay also includes use of the Sunset Bay marina, pool and fitness areas. Come. Enjoy! Note: This property does not have a boat slip, however, use of the marina is included. 7-night minimum stay is required during all seasons. brbr- SPECIAL NOTE: This rental home has a 7 night minimum year 'round. 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.

Sunset Bay Villa 206 | Luxury Condo w/ Waterside Balcony, Gourmet Kitchen + Pool & Fitness

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$246.2

Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Painted Pony Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern Amenities, there's no better home base for making Chincoteague Island Vacation Memories. brbrAs you pull up to this whimsical Cottage, the White Picket Fence and Sea Glass Blue Door are so welcoming. You can already feel yourself relaxing. Just the thought of sipping Sweet Tea on that Screened Porch - you can hardly wait. Located in the heart of Chincoteague Island on Willow Street, you are tucked away in a quiet location, yet close to everywhere you want to be. Walk to the Carnival Grounds in July to enjoy our famous Firemen's Carnival, and visit the ponies penned up just a short walk from the Cottage. brbrThere is ample parking for 3 Cars just behind the house, off of Willow Street. As you enter Painted Pony Cottage, fond memories of Grandma's house may come back to you - it just feels so comfy and full of love. The spacious Kitchen has Warm Knotty Pine Cabinets and lots of Countertop space. The Chef in the family will be pleased with how well-stocked it is. Dine indoors at the colorful Kitchen Table, or Al Fresco at the Picnic Table in the backyard - a great place to enjoy some of our Fresh Local Crabs! brbrAs you wander to the Living Area, you'll fall madly in love with the Rustic Hardwood Floors throughout the Cottage. Relax after a fun-filled day at the Beach in the AC, and enjoy the Free WiFi and Flat Screen Streaming TV. Colors of Sunshine and Blue Sea are so bright and cheerful - it's just a great room to spend time in. Just off the Living Area lining the front of the Cottage is a fabulous Screened Porch with relaxing Rockers and Gliders - a wonderful place to gather in the evening and share stories of the day's adventures. Watch the kids play safely in the Fenced-in Front Yard, which Fido will appreciate, as well!brbrPainted Pony Cottage sleeps 6 more than comfortably in 3 Bedrooms, with a Full Sleeper in the Living Area. The Master Bedroom is on the 1st Floor and is also the only access to the Full Bathroom. Adorned in Nautical Navy and White, it is bright and cheerful, and has a comfy Full Bed. The shared Full Bath has a Tub/Shower Combo, and although you access it through the Bedroom, it is quite convenient for all. Fun painted pony decor greets you, keeping this awesome theme going throughout the Cottage. Watch your head as you follow the Winding Wood Stairs upstairs to Bedrooms 2 and 3. There are 2 Twins in Bedroom 2, and another Twin in Bedroom 3. This is an awesome place for the kids, who will feel like they have their own private hideaway. brbrPainted Pony Cottage - The perfect place to Relax and Reconnect with those who matter most in this life........brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Friendly dogs welcome with $100 Pet Fee. Dogs MUST be current on Flea/Tick Preventative and Immunizations. No Cats.

Painted Pony Cottage by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$205.68

Peace. Love. Beach.brbrHave you been yearning for a break from the hectic day to day An affordable getaway that will bring those together who matter most - and without breaking the bank We’ve got you covered - take a look at One Peace Cottage on beautiful Chincoteague Island - where our Wild Ponies roam free, and there’s not a high-rise building to be found. Just natural beauty and a peaceful paradise…..brbrA visit to One Peace Cottage is like coming home to visit an old friend. Modest, yet so charming, this one-level home sits on Deep Hole Road, in the very heart of Chincoteague Island. You’re just 5 minutes from Assateague National Seashore, and a hop, skip, and jump from Restaurants, Shops, and Entertainment. brbrYou’ll love relaxing in the cozy Living Area and enjoying Free WiFi and Flat Screen Cable TV with Streaming. It’s perfect for kicking back after a day of fun in the sun at the Beach, and sharing stories of the day’s adventures. If you’re more of an Outdoorsy person, you may never want to leave the Screened Porch. With Colors of Sea Glass and Sand Dunes, you’ll love just “being” and listening to the Tree Frogs sing. And there's a Picnic Table for enjoying some Fresh Local Crabs!brbrThe Chef in your family will find mealtime a bay breeze in the well-stocked Kitchen. Dine in the comfort of Central AC, or on the Screened Porch. Not one to cook on Vacation You’re just steps from Gary Howard Seafood, Captain Zack’s Seafood, and many other great Dining options!brbrOne Peace Cottage sleeps 8 in 3 Bedrooms and with 2 Full Baths. The Master Bedroom is dressed in Pale Blues and Beige, and has a King Bed, and Flat Screen TV. The attached Private Master Bath has a Tub/Shower Combo. On the other side of the house, you’ll find Bedroom 2 with a Queen Bed, and Bedroom 3 with a very cool Full over Full Bunkbed! There’s also a Sleeper Sofa in the Living Area, just to give you another option. Full Bath 2 also has a Tub/Shower Combo. brbrWe just love homes that combine all of that quintessential Chincoteague Charm we love - like a visit to Grandma’s house - with the Modern Amenities you want and need. And don’t forget to bring the Boat! With a huge Concrete Driveway, there’s plenty of room for your vehicles and your Boat on its trailer. And there are several Boat Launches available very closeby. So, if you’re looking for adorable and affordable, give us a call - find some peace today at One Peace Cottage on our beautiful Little Island by the Sea!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.

One Peace Cottage by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$281.25

Rest A' Shored is a brand new home (2019) with a sweeping, open floor plan that can comfortably accommodate two families with children, or three couples for your island retreat. Located on Willow Street, the property is just a short walk to Main Street and the Chincoteague Fair Grounds, right in the heart of the pony penning action! The house provides all the modern amenities needed for your stay, with a touch of Chincoteague charm. The kitchen is well equipped with everything you need to cook for a crowd! Granite counters, 2 refrigerators, dishwasher, plenty of pots, pans, serving utensils, crockpot, electric griddle, even a blender for all those mixed drinks! Enjoy family meals at the dining room table which comfortably seats 8, plus an additional 5 at the bar top on the kitchen island. A large screened in porch can accommodate all your guests to enjoy meals outdoors, or relax with a cocktail and feel the cool evening breeze! Designed with families in mind, beach chairs, umbrellas, and toys are available for use for sunny days on the beach. For those rainy days, the large living room sectional is perfect for snuggling up to catch a movie! Highspeed internet is available, with multiple TVs, and Microsoft X box in the kids room to play any video games you bring with you (You would need to bring your own controllers and games). For the small ones, a pack and play is available for your use. This is a dog friendly home as we know they are part of your family! (extra pet fee applies)A large driveway provides plenty of parking for up to six passenger vehicles.

Charming Chincoteague getaway, short walk to the fair grounds and pony penning!

Chincoteague Island, Virginia, United States

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Bath

Sleeps

$767.05

Moorings North is an unique architecturally designed five bedroom home in the heart of Chincoteague Island, VA. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a coffee house, and restaurants.brbrThis elegant, but cozy home is an ideal waterfront vacation spot for families as well as for couples who are seeking a romantic getaway.brbrBe our guest at Moorings North and enjoy your vacation in a beautiful setting with nearby award winning beaches and wildlife refuges.brbrTwo-story porches grace the front of this dynamic house from where you will enjoy the rising sun. You will enter a light filled two-and-a-half story high entrance hall with a grand staircase, and French chandelier. Ascending the stairs, you’ll be delighted along the way by the views to the water from three towering windows, or take the convenient windowed elevator to the living level on the upper floor.brbrWith the reverse floor plan the upper level is the main living level including the great room with beverage bar, kitchen, master bedroom, and a full bathroom.brbrArriving in the great room your eye (and your heart) will quickly be drawn to what you’re here for: a wall of nine windows will open up sweeping views of sun-diamonds dancing on the sparkling waters of Chincoteague Bay. Simply stunning!brbrThe great room is combined with the dining area and an open concept kitchen, which invites you to entertain yourself, your family and your friends. The towering cathedral ceiling in the great room will give you a sense of space and open feeling on hot summer days as well as a cozy atmosphere by the gas fireplace during your relaxing winter vacation. You’ll enjoy preparing locally caught seafood in the fully appointed gourmet kitchen. Two ovens, warming drawer, microwave, dishwasher, granite counter tops and more are waiting for you. While some gather around the large screen plasma TV on the fireplace wall, one or two may prepare drinks at the beverage center.brbrThe spacious kitchen with its cherry cabinets and granite counter tops is sure to be a popular spot to entertain. There is plenty of room to pitch-in for cocktail and canapé, or prepare a delicious supper of fresh seafood purchased at the town dock.brbrWhile the house has two climate control systems, there will be days when you will want to open the French doors leading from the dining area to the columned, covered Gazebo-in-The-Sky: outdoor relaxation sublime high above the sparkling waters. Here, it’s likely you will linger (probably everyday) while the sky turns shades of magenta and orange as the sun descends into the bay. In this amazing outdoor living space you’ll find a gas grill to bring even your cooking outdoors, a dining and a conversation set.brbrUp a spiral stair from the Main Level is the Tower-Hide-Away with three additional twin beds, just right for the young, and the young-at-heart. The view from the highest point of the house over the waters are indeed again breathtaking. Tower guests share bath on Main Level.brbrAt the end of your day on Assateague Island’s pristine ocean beach (or perhaps you climbed to the top of the lighthouse ) you’ll be ready to enjoy a great night’s rest in your private quarters on the Lower Level. Because there are two master suites, each equally tasteful decorated rooms with king-size bed, granite top make-up vanity, walk in closet, bathroom with separate tub, and walk in shower, perhaps there won’t be any trouble over ‘who-gets-to-sleep-where’.brbrA word about the bathrooms: one has a large Kohler soaking tub, the other one has a Kohler whirlpool tub for two. Did we mention that each of these suites has a private balcony over the water brbrOn this level there’s a room with a queen size bed, and an ensuite bath with water view window in the shower.brbrAs many of the houses on the coastline Moorings North is elevated, which will give you extra storage space on a partially enclosed ground level and direct water access. Tie your up to 65’ long boat up in deep water at our bulk-headed dock right there. Catch your all time fresh crabs and fish right from the dock. How much fun will it be for children and grown-ups to provide your seafood dinner right from the water in front of your vacation residence Enjoy your summer evenings in the private sitting area, where you can roast s’mores at the fire pit. You hardly want to leave your vacation spot right on the water of Chincoteague Channel, but in case you would like to spend a day at the beach, we’ll provide beach chairs, sun umbrella and boogie boards for you. When you come back from a beautiful day on the beach, enjoy the convenience of an outdoor shower. From the ground level there is an elevator entrance handy for handling luggage and bringing in the groceries. This elevator makes all floors handicapped accessible.brbrStill some energy left Take one of the four bikes and explore the many attractions Chincoteague Island has to offer.brbrWe will do whatever is in our hands to make your vacation time at Moorings North exceptional, comfortable, and unforgettable. We welcome you to our well-loved home on Chincoteague Island!

Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$248.27

Live your Life by a compass, not a clock…..br brWork, school, traffic, homework, repeat - right ! It’s time for a break - a Beach Break, that is! Get ready to relax, unwind, and simply….be. Be with those who matter most - giggle, frolic on the Beach, and make memories that will forever be treasured. Breathe - you’re on Island Time now. And boy, do we have the perfect place for you - Happy Hideaway on Chincoteague Island!brbrThis adorable home has been a super popular Vacation Home for years, previously known as “Flew the Coop”. Tucked on a quiet street in Piney Island, which happens to be the closest community to Assateague National Seashore, you can ride your bike or even walk to the Beach! brbrWhether your pleasure is searching for our famous Wild Ponies, shell combing, climbing the Lighthouse, or just chillaxing, this is the place to be. 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.....brbrNow let us tell you a little about ‘Happy Hideaway’, and we will lead with, you’ll never want to leave this adorable Chincoteague Cottage. As you pull down Oak Drive, Happy Hideaway, adorned in red, boldly welcomes you to Piney Island. Surrounded by whispering Oaks, just imagine sitting on the Porch feeling that sea breeze while listening to the Tree Frogs sing. Upon entering, you will find Happy Hideaway to be every bit as captivating with bold blues, distressed wood, and a fabulous beach decor. brbrYou’ll love kicking back in the Living Area after exploring Assateague, and enjoying Free WiFi and Flat Screen Streaming TV. The Open Layout is perfect for spending time together without ever feeling crowded. Prepare family meals easily in the Well-Stocked Kitchen - grill the Fresh Catch of the Day on the Charcoal Grill, or just grab a quick bite before hitting the Beach. With Stainless Appliances and a Farmhouse Sink, mealtime will be a bay breeze. Not one to cook on Vacation You can stroll to several of our most popular dining venues including Famous Pizza, Woody’s Barbecue, and Lily’s Little Mexico - yum! When the time comes to enjoy some Fresh Local Crabs, the huge Screened Porch at Happy Hideaway is the place to be. With plenty of seating for everything from dining Al-Fresco to relaxing and sharing stories of the day’s adventures, you’ll love an evening spent there under the beachy white lights. brbrHappy Hideaway sleeps 8 more than comfortably in 3 Bedrooms and 2 Full Baths. The Master Bedroom with a Queen Bed is beyond charming with Rustic Barn Doors, cool grays, and crisp whites. The Private Master Bath currently has a Claw Foot Tub, but will have a Brand New Tub/Shower Combo for Summer 2022! On the other side of the house, you’ll find 2 more Bedrooms and another Full Bath. Full Bath 2 currently has a Walk-in Shower, but will also have a Brand New Tub/Shower Combo for Summer 2022! Bedroom 2 has colors of sea glass, a comfy Queen Bed, and another Flat Screen Streaming TV. Right next door, Bedroom 3 is perfect for the kiddos with 2 sets of Twin Bunkbeds (4 Twin Beds), and a fun tropical theme. Speaking of the kiddos, did we mention that Maui Jack’s Waterpark is a short walk away brbrPiney Island is the epitome of peaceful bliss - this wonderful community has quiet, tree-lined streets perfect for long walks in the morning. There is even a Natural Kayak Launch just around the bend, so bring your kayaks or rent some for your stay! If you’re looking to forget the real world - just for a little while - Happy Hideaway is the place for you. 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.

Happy Hideaway by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$296.61

Welcome to Cozy Nest, a charming home available for your next vacation experience, offering an idyllic retreat with stunning water views! This inviting property spanning over 900 sq. feet can accommodate up to 6 guests, making it an ideal choice for families, friends, or anyone looking to immerse themselves in comfort and tranquility.brbr brbrCozy Nest features two well-appointed bedrooms and two full bathrooms, ensuring privacy and convenience. The primary suite bedroom, encompassing the entire second floor, offers a peaceful haven for relaxation with its serene views, private bath, and private deck access. The first floor provides flexible sleeping arrangements with two twin beds in the bedroom, and a sleeper sofa in the living room. The full bath on the first floor rounds out the convenient layout.brbr brbrThe heart of this home is its beautiful outdoor spaces. A screened porch provides a bug-free zone to enjoy the fresh air and scenic surroundings, while the open deck invites you to bask in the sun, stargaze at night, or dine al fresco against the backdrop of picturesque water views. These outdoor areas are perfect for entertaining or simply unwinding after a day's adventures.brbr brbrPet lovers will be delighted to know that Cozy Nest is pet-friendly, and welcomes your furry friends to join in on the family fun. Additionally, with three parking spaces available, guests will find ample parking for their vehicles.brbr brbrLocated in a serene setting with captivating water views, this property offers the perfect blend of relaxation and convenience. Whether you're seeking a peaceful getaway or a comfortable base from which to explore the area, Cozy Nest promises a memorable stay for all who visit.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. 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.

Cozy Nest | Water View Retreat w/ Screened Porch, Private Deck Suite & Pet Friendly Comfort for 6

Chincoteague Island, Virginia, United States

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