Vacation Rentals By Owner In Chincoteague Island, VA

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

$174.39

Have you always wanted to Vacation on Chincoteague Island, but couldn't bear the thought of 4 of you in a hotel room Love the idea of a Vacation Home, but don't want to break the bank Look no further than Sunrise Serenade at Sea Tag Lodge, formerly Sea Tag # 24. These fabulous Condos are located directly on the Assateague Channel with some of the most breathtaking Views to be had. Just imagine relaxing on your Waterfront Balcony and seeing our famous Wild Ponies roaming in the Marsh across the Channel. There is something for absolutely everyone in your family at Sunrise Serenade!brbrThis delightful and affordable 2nd Floor Condo sleeps 4 and is an end-unit, offering even more sweeping views and privacy. Relax in the cool comfort of the Living Area after a fun-filled day on the Beach, and enjoy the large Flat Screen Satellite TV and even Free WiFi, while taking in phenomenal Water Views right from the comfort of the sofa! Decorated in classic Beach Cottage style, you will love the white washed knotty-pine walls that are reminiscent of strolling on a Boardwalk. brbrThe Kitchen features new Solid Surface Countertops and is well-stocked with everything you need to prepare family meals or whip up some fresh Chincoteague Seafood. Hopefully you will be cooking up some fresh fish, crabs, or clams you caught right from the Private Dock! A Charcoal Grill is also provided in the picnic area if grilling is your thing. You'll love dining Al-Fresco on the Balcony while taking in one of our famous Chincoteague Sunsets, or stay cool indoors in the Dining Area.brbrThe Master Bedroom features a Queen Bed and another large Flat Screen Satellite TV, and is beautifully decorated in colors of Sand and Sea. In the Living Area, there is a Brand New (2019) Queen Sleeper Sofa - absolutely perfect!. A spacious Full Bathroom has a Tub/Shower Combo and is adorned in colors of the sun setting over the Bay. Sea Tag Lodge has on-site Pay Laundry for your convenience, as well. brbrSunrise Serenade also comes with a Private Boat Slip that will accommodate up to a 25 foot boat! And if you happen to be coming for our famous Chincoteague Pony Swim, you truly cannot ask for a better location - you won't even have to leave your Balcony! Traveling with friends or extended family Also check out its sister home, Sunrise Sonata, located on the 1st Floor directly below Sunrise Serenade.brbrSunrise Serenade - Playing the songs you want to hear on your Chincoteague Island Vacation!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Building has Exterior Security Cameras.

Condo

Sunrise Serenade 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

$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

$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

$244.46

Cute, clean, and chic — this cozy one-bedroom, one-bathroom studio apartment has everything you need for easy island living on Chincoteague. Whether you're looking for a seasonal escape or a place to call your home away from home, this little gem delivers big on charm without the fuss.brbrStep inside to find a full kitchen ready for your culinary adventures — from simple morning coffee to a full-blown seafood feast after a day at the beach. Full laundry is conveniently right on-site. It's the kind of place where you can kick off your sandals and just breathe.brbrConveniently located near the carnival grounds and South Main Street, you're never far from the heart of island life. Veteran's Memorial Park is just a short stroll away for those peaceful morning walks. Need groceries Island Foods Great Valu is right up the road. Feeling adventurous Maui Jack's Waterpark and the stunning Assateague Beach are both within easy reach for endless fun in the sun.brbrHere's a fun bonus — this apartment is attached to a charming property affectionately known as Grandma's House, which is available as a separate rental. Rent them together for a larger group or keep things simple and snag just this spot for yourself.brbrIsland living doesn't have to be complicated. Sometimes all you need is a cozy space, good vibes, and the sound of the ocean breeze. Come see what Chincoteague living is all about!brbr- Linens and towels are included with your reservation. br- No smoking is permitted on the premises. br- No pets are permitted on the premisesbr- 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.

Apartment

Grandpa's Cottage | Cute, clean and cozy studio apartment!

Chincoteague Island, Virginia, United States

Bed

Bath

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

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

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

Bath

Sleeps

$197.04

Charming island cottage ideally located close to downtown shops, restaurants, and the park. This inviting, single-level home features a spacious backyard with a brick patio, built-in fire pit, and a private enclosed outdoor shower - perfect for relaxing after a day out.brbrInside, the open living area features a comfortable living room with a breakfast bar that seamlessly transitions into the fully equipped kitchen. The cottage includes two bedrooms: one with a queen bed and a convenient half bath, and a second bedroom with two twin beds. A full bathroom with a shower is located in the hallway of the home.

Cottage

Sidewalk's End- Quiet Street, Close to Everything

Chincoteague Island, Virginia, United States

Bed

Bath

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

$303.3

Waterfront retreat with lighthouse views, wild ponies, and stunning sunrises. Wake up to sweeping vistas of the water, the iconic lighthouse, and, if you're lucky, a glimpse of wild ponies grazing across the marsh. Each morning brings a spectacular sunrise best enjoyed from the comfort of your screened porch.brbrThis serene Eastside getaway offers the perfect blend of nature, comfort, and convenience for families, couples, or remote workers. The second-story unit features a cozy living room, dining area, and fully equipped kitchen. The primary waterfront bedroom has a queen bed, an ensuite bath, and direct access to the screened porch. A second bedroom with two twin beds is located across from a full hallway bathroom.brbrThe screened porch is ideal for morning coffee or evening drinks, and a shared dock provides opportunities for crabbing, birdwatching, or launching kayaks into the calm waters. Enjoy prime wildlife viewing, including wild ponies, coastal birds, and ever-changing lighthouse vistas.brbrJust minutes from Chincoteague’s shops, restaurants, and beach-town fun, this retreat is perfect for relaxing, exploring, or simply soaking in the coastal charm. Please note, no boat dockage is available at Wonderview units; guests may bring and launch their own kayaks, but they must be stored on their vehicle, not on the grounds or property.

Condo

Wonderview #202- Waterfront with Lighthouse & Assateague Views

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

$540.19

Island Days and Sunny Rays…..brbrWelcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous Condos sit directly on the Bay with stunning Views of the Bay, Marsh, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop and dine in the Historic District. ‘Our Pleasure’- Sunset Bay 306 - offers the Luxury you want, the Amenities you need, and Bay Views that will leave you breathless, all at a family-friendly price! AND, you’re welcome to bring the family dog with NO Pet Fee (1 Dog under 35 lbs only). Traveling with a larger group You can rent Sunset Bay 306 and 307 - right next door!brbrYou’ll feel a million miles away from the real world, yet still be close to everywhere you want to be - including Assateague National Seashore, where our famous Wild Ponies roam free! Whether you enjoy searching for Wild Ponies, Beach Combing, Fishing, or just Sunbathing, there’s truly something for everyone in your crew. Our Beaches are wild and wonderful - no highrises, no boardwalks - just beautiful Mother Nature! 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 kick off your Flip Flops in ‘Our Pleasure’s’ spacious Foyer, you’ll be welcomed by Colors of Sand and Sea - muted tones pulled from Nature itself, creating a warm, peaceful, and oh, so welcoming retreat. This Newly Renovated Condo has THE most awesome layout for spending time together, without ever feeling crowded. brbrRelax in the spacious Living Area after a fun-filled day at the Beach, and enjoy Free WiFi, Flat Screen Cable TV with Streaming, and Views that will knock your socks off. With plenty of comfy furnishings, it’s truly a “home away from home”. Stroll out to the Waterfront Balcony and watch Herons, Eagles, and Egrets fish for their morning meal, or enjoy watching children fish and crab from the Dock below - what a wonderful place to begin and end every precious Vacation Day!brbrThe Chef in your family will appreciate the Well-Stocked Kitchen with everything you need to make mealtime a bay breeze. Dine in the comfort of Central AC in the Dining Area, or Al-Fresco with a Bay View on the Waterfront Balcony. Not one to cook on Vacation No worries at all - there are many great Dining options just a hop, skip, and jump away! brbrOur Pleasure sleeps 7 in pure comfort and style in 3 Bedrooms. We love the “split floorplan” of this wonderful Condo, with the Primary Bedroom sitting Waterfront on one side, and Bedrooms 2 and 3 on the other side, offering more privacy to all. brbrBedroom 1 is the Primary Bedroom and has a luxurious King Bed, and awe-inspiring Views that you will have the pleasure of waking up to each morning! With 2 walls of windows to the Water, Private Balcony Access, and Flat Screen TV, it’s truly a retreat. The spa-like Private Attached Bath has a Double Vanity, Custom Tile Walk-in Shower, and Soaking Tub - pure heaven. brbrDown the Hall, you’ll find Bedrooms 2 and 3, plus a 2nd Full Bath. Bedroom 2 has a comfy Queen Bed, Flat Screen TV, and lovely Bay Views. Bedroom 3 is perfect for the kiddos - or the singles - with 1 Twin Bed and 1 Full Bed. Full Bath 2 is convenient to both, as well as the Living Area, and has a Tub/Shower Combo. A Full Size Washer and Dryer is provided for your convenience, as well. brbrIf you aren’t already in love with the gorgeous interior of Our Pleasure, just wait until you hear about the Outdoor Living at this fabulous Community! With access to Sunset Bay’s Pier/Dock, you can try your hand at Fishing and Crabbing, or bring along your kayaks! Not to mention Sunset Bay’s alluring Outdoor Pool sits right on the Bay with incredible Views and salty bay breezes. And if you think you’ve had a bit too much fun at the Island Creamery (an absolute must), you can work it off a little at the Community Fitness Center, just downstairs. Whatever your pleasure, Our Pleasure is ready to make it happen!brbr*Seasonal Outdoor Pool - dates subject to change*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.

Condo

Sunset Bay 306 by Seaside Vacations & Sales

Chincoteague Island, Virginia, United States

Bed

Bath

Sleeps

$224.58

Welcome to this charming bungalow located in the center of Chincoteague Island! This delightful house offers a cozy and comfortable living space, making it the perfect place to call home. With 1 bedroom and 1 bathroom, this property is ideal for individuals or a small family looking for a serene retreat. As you step inside, the throw-back retro kitchen adds character to the home and makes cooking an enjoyable experience. Whip up your favorite meals while reminiscing about the good old days. The kitchen is equipped with all the necessary appliances to satisfy your culinary desires. You'll be greeted by the warmth of the main bedroom featuring a comfortable queen bed. The second sleep area serves as both a sleeping and an office space, with a twin pull-out sofa providing versatile accommodation options. Whether you work remotely or simply need a quiet space to focus, this flexible layout has got you covered! The bungalow is close to town and 'Beach Road' - convenience is at your fingertips. Enjoy easy access to local amenities such as shops, restaurants, and entertainment options. Whether you're in the mood for a leisurely stroll or need to run some errands, everything is just a short distance away. After a long day, relax and unwind in the enclosed front porch. This inviting space is perfect for enjoying your morning coffee or savoring a glass of wine in the evening breeze. Additionally, there's an outside shower, allowing you to rinse off after spending time at the nearby beach. With parking spaces for 2 vehicles, parking won't be a hassle. Don't miss out on the opportunity to make this charming bungalow your next vacation spot! With its convenient location, versatile layout, and retro charm, it's sure to steal your heart.brbr- *NEW FOR 2025: Level 2 EV charger!*br- 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. Small dogs only, restricted to two (2) pets. 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.

Cottage

Blue Crab Bungalow | In-Town Chincoteague Retreat w/ Enclosed Porch, EV Charger & Pet Friendly

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