Vacation Home Rentals By Owner In Chincoteague, VA

Enjoy stunning views from this classic Waterman’s-style home, completely gutted, lovingly restored, and thoughtfully updated for modern comfort. Take in fantastic sunset views from the front enclosed porch, which features both AC and heat for year-round enjoyment. The rear deck overlooks a fenced backyard, perfect for relaxing or playing. A gas grill and cornhole set are provided for outdoor fun.brbrFirst Floor Features:brA fully equipped kitchen opens to the dining room and a cozy living room. The semi-private den can double as a main-level sleeping area. A full bathroom with a walk-in shower and a laundry area are conveniently located off the kitchen.brbrSecond Floor Features:brThe first bedroom includes a king bed. The second bedroom offers beautiful water views and also features a king bed. A shared full hallway bathroom provides a tub/shower combo. A small office nook with a view completes the upper level—perfect for reading, writing, or remote work.brbrPlease note that the Third bedroom is a private den on the the First Floor.

Island Time- 3BR Home | Water View Chincoteague Bay

Chincoteague, Virginia, United States

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$227.51

Amenities: Central A/C, Cable TV (Basic Cable), WiFi, Dishwasher, Microwave, W/D, Wood Burning Stove (seasonal), Screen Porch, Enclosed Porch, Outside ShowerbrbrLooking for the perfect lake view vacation home, Sandy Moose is it! This home is located in Oyster Bay II and is sure to please the whole family! Enjoy a day at the beach then sit back and enjoy the water-views of Mallard Pond from the screened in porch. Newly remodeled with granite counter tops and Pergo flooring. Home has security camera under the house directed towards the pond. brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrLINENS AND TOWELS PROVIDEDbrbrBed Sizes: 1 King, 1Queen, 1 Double Sleep Sofa, 2 Twinsbr brSaturday Change Overbrbr2026 Prime Season Rate $ 1400 per week / $ 200 per night br2026 Pony Swim Week $ 1603 per weekbr2026 Off Season Rates $ 1106 per week / $ 158 per night with 3 night minimumbrbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Sandy Moose - 3BRWaterfront home on lake, screened porch, LINENS AND TOWELS

Chincoteague, Virginia, United States

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Select Dates for Price

Looking for an incredible Chincoteague Island Vacation Experience You just found it at Sea Treasure - a beautiful Duplex that sleeps 6 more than comfortably in the very heart of our special Island. Located on Ridge Road, right next to famous Pony Swim Lane, you can relax on your Screened Porch and take in amazing Views of Assateague Island and our Famous Wild Ponies. You can even watch the Pony Swim without leaving your chair! Have a larger family or traveling with a group Sea Mist, Sea Treasure's Sister Home, is right next door. These gorgeous Homes share amazing Views, but offer privacy, as well. Just a short stroll from Memorial Park, you're in the right location for all sorts of family fun!brbrAs you pull into the driveway, you can already catch a glimpse of the water - even when it's not Pony Swim, you can feel the excitement of this location and all it has to offer. Sea Treasure has a wonderful Open Layout - spend time with those you love without ever feeling crowded. Take in those Assateague Island Views from almost every room in the house - even the Kitchen! Speaking of which, the Chef in your family will love how light, bright, and well-stocked it is. Enjoy meals in the spacious Dining Area, or dine Al Fresco on the Screened Porch and take in that salty, sweet sea breeze. brbrYou'll love relaxing in the casual and comfortable Living Area with Free WiFi and Flat Screen smart TV/DVD. Or curl up with a good book on the Porch and listen to the Tree Frogs sing. Just imagine morning coffee here as you watch the Herons and Egrets fish for their morning meal, or some Ponies wading in the Marsh. After a fun-filled day exploring Assateague National Seashore, just a few minutes away, it really doesn't get much more relaxing than this! Also on the 1st Floor is a convenient Half Bath and Laundry Room. brbrWandering upstairs you'll find 2 spacious Bedrooms and a Full Bath. Bedroom 1 has a comfy Queen Bed and a Private Water View Balcony - just wait until you see the Views from up here! Sneak out and watch the Sunrise while everyone else slumbers for a very special Chincoteague Experience, or stargaze while listening to the trees swaying in the breeze. Down the Hall, Bedroom 2 has another Queen and colors of Sea Glass - peaceful and serence. There is also a Full Bath with Tub/Shower Combo convenient to both Bedrooms. brbrThe Outdoor Living at Sea Treasure is just as awesome - stroll down the street to Memorial Park where you can launch your kayak, play on the playground, or even do some crabbing and fishing! After a day of shell-combing and pony hunting, rinse off in the refreshing Outdoor Shower and then grill the Fresh Catch of the Day while listening to the birds sing. Whatever your pleasure, we've got the place - plan your island-time today! Rent Sea Mist and Sea Treasure together for a fabulous Family Reunion or Multi-Family Getaway!brbr*Please note Dock seen in pics is not part of this property and is private property. brbrSea Treasure - Beach Memories last a Lifetime.....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.

Sea Treasure by Seaside Vacations & Sales

Chincoteague, Virginia, United States

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$262.59

Welcome to beautiful Saltwater Cottage, in the heart of Chincoteague Island, Virginia. You've heard stories about our little piece of Paradise - the Wild Ponies running free, Saltwater Cowboys leading the way, the Saltiest, Sweetest Oysters to be found, and hands down THE best Sunsets over the water. Guess what It's ALL true - isn't it time you discover this incredble Vacation Destination ! brbrThis adorable Cottage is located on Anderton, just off of Church Street - a super short stroll to Main Street, where many Shops and Restaurants are located, as well as Robert Reed Waterfront Park - a fabulous place to take in one of our famous Sunsets! brbrAs you enter the Cottage, you'll know you made the right choice. Beautifully decorated with a tasteful Coastal Flair, the soothing Colors of Sand & Sea are both serene and refreshing. Relax in the spacious Living Area after a fun-filled day on the Beach and enjoy the Free WiFi and Flat Screen TV with Streaming. With a wonderful Open Floor Plan, the whole gang can reconnect without ever feeling crowded. With New Floors reminiscent of the Boardwalk you grew up visiting, Exposed Ceiling Beams, and splashes of blue that make you feel like you're still there, you may not want to leave.brbrThe Chef in your family will love the well-stocked Kitchen with tons of space AND tons of gadgets. Enjoy meals with the family here, at the Breakfast Bar, or Al-Fresco on the huge Porch. There's even another Picnic Table outside for enjoying those Local Crabs you've been craving! Fido will love the spacious yard for sunning in, as well as the porch, and the Cottage is in a great location for taking long walks with your pup. brbrAt the end of a fabulous day exploring Paradise, relax on the Porch and share stories of the day's Adventures while listening to the Tree Frog's sing. These are the memories that stay with you forever.....brbrDown the Hall, the stunning Master Bedroom has a luxurious King Bed and Private Master Bath. So many special touches, such as the double French Doors leading to the gorgeous Master Bath with Granite Vanity, will make you feel pampered. On the other side of Saltwater Cottage, there are 2 more Bedrooms with brand new everything! Bedroom 2 is perfect for the kids with 2 Twin Beds and Nautical Navy and Crisp White décor. Bedroom 3 has a comfy Queen Bed waiting for you, as well as a beach Seashell Theme in cool Coastal Colors. brbrThe perfect Vacation Home, the perfect Location, all at the perfect Price - AND, your pup will be perfectly content to be able to join in on the family fun! LIMIT 1 DOG.brSaltwater Cottage - Because Memories made at the Beach last forever......brbrOne Dog welcome at no add'l charge - must be pre-approved, and current on vaccinations and flea/tick preventative. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.

Saltwater Cottage by Seaside Vacations & Sales

Chincoteague, Virginia, United States

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$285.09

Welcome to Seaside Serendipity - where happiness comes in waves.... brbrLooking for the perfect beach getaway for your family You’ve serendipitously stumbled upon THE place to be on Chincoteague Island. This adorable Water View Home has to be in one of the best locations on our beautiful little island. Located adjacent to ever-popular Veteran’s Memorial Park, the world is your oyster. Only steps away, you will find a fabulous playground, pier for fishing and crabbing, tennis and basketball courts, and a boat launch ideal for launching kayaks, as well as boats. brbrSeaside Serendipity has all of this - and at a family-friendly price tag. Just imagine enjoying your morning coffee on the Deck while watching Herons and Egrets dance over the Assateague Channel. Or stroll down to the dock to try your hand at fishing and crabbing. And you can enjoy a glass of pinot while watching the kids safely playing at the playground, just across the lane from the house. There's even a Brand New Outdoor Shower for rinsing off sandy feet.brbrUpon entering, the colors of sand and sea relax you immediately. With lots of natural light and soaring ceilings, this cozy home feels so open and airy. Unwind in the Living Area after a fun-filled day at the beach and enjoy the Flat Screen TV with Apple Streaming and Free WiFi. Just off the Living Area, the well-equipped Kitchen makes mealtime a bay breeze. There’s plenty of room for all at the Dining Table and Breakfast Bar, or wander down the street to Etta’s Channelside Restaurant, or super popular Mr. Baldy’s. Enjoy the bay breeze as you dine on some Local Crabs outside at the picnic table. There is also a Brand New Full Bath with Walk-in Shower and Full Size Washer and Dryer just off the Kitchen. brbrSeaside Serendipity sleeps 8 in 3 comfortable bedrooms. On the 1st floor, Bedroom 1 has a Queen Bed. Wandering upstairs, you’ll find 2 more Bedrooms and a Full Bath with Tub/Shower Combo. Bedroom 2 has another Queen Bed, and Bedroom 3 sleeps 4 in 2 sets of Bunk Beds. With this family-friendly layout, it would even be perfect for 2 small families to share!brbrThis fabulous home is about soooo much more than where you lay your head at night. Seaside Serendipity is truly a vacation experience. With so much to do, right outside your door, boredom will never be an issue! Book your time in paradise today! Traveling with another family ! Book Seaside Serendipity and Channel View Charmer, right next door, together!brbrNo Pets/No Smoking. 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. Home has exterior security cameras.

Seaside Serendipity by Seaside Vacations & Sales

Chincoteague, Virginia, United States

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$415.43

Of all the paths you take in life, make sure a few of them are sandy…..brbrWelcome to ‘Paradise’ on dreamy Chincoteague Island - it’s not just a vacation home, it’s a feeling - relax, rejuvenate, and reconnect with those who matter most at this gorgeous Waterfront Townhome nestled directly on the Chincoteague Bay.brbrTucked away in the perfect location on South Main, Paradise directly faces THE most incredible sunsets. Just imagine sipping your morning coffee and watching Herons, Egrets, and even Dolphin fish for their morning meal. With 3 levels of Waterfront Balconies, the toughest decision will be which one to relax on! This 3 Bedroom dream home also has a Community Pier and access to the Pool across the street at The Birchwood Hotel. brbrAfter a fun-filled day exploring Assateague National Seashore - home of our famous Wild Ponies - you’ll love sinking into the comfy Living Room furnishings and enjoying Free WiFi and Streaming TV. And you won’t believe the incredible Bay Views - right from your sofa! There’s plenty of room for all to gather and share stories of the day’s adventures. brbrThe Chef in your family will just love the Gourmet Kitchen with Stainless Appliances, Gleaming Granite Countertops, and Tile Flooring. With all the bells and whistles, preparing family meals will feel anything but a chore, and you can take in those amazing views even from there. Dine in the comfort of the Central AC, or wander to one of many Dining options just a hop, skip, and jump away. Paradise is also located steps away from our famous Carnival Grounds, where you can have a blast at the Fireman’s Carnival every weekend the entire month of July. Boy, this would be a great location if you’re planning to come for the Pony Swim, as well!brbrParadise sleeps 6 in 3 Bedrooms plus a Sleeper Sofa in the Living Area. Bedrooms 1 and 2 are located on the 1st Floor, and share a Full Bath with Tub/Shower Combo. Bedroom 1 has1 twin and 1 Full and pretty shades of sand and sea. Bedroom 2 has a comfy Queen Bed, and sliders leading out the breathtaking Views on the Waterfront Balcony. The spacious Full Bath has Double Sinks, lovely Marble, and a separate area with the Tub/Shower Combo. There is also a Full Sleeper Sofa tucked in an alcove on this floor.brbrWandering up to the 3rd Floor, you’ll find the luxurious Master Suite with King Bed and stunning Bay Views that go on forever. The Spa-like Master Bath is that of a 5 Star Hotel with a relaxing Soaking Tub, Walk-in Shower, and gorgeous Vanity. brbrBut life at Paradise isn’t all about what’s inside - right outside your door is a veritable waterfront playground! Just imagine catching crabs and fish right in your own backyard. Launch your kayaks and explore our many sandbars at low tide, or bring the boat! We may be able to arrange for use of a Boat Slip during your stay - just ask! And if it’s too windy for the beach, you can wander across the street and enjoy the pool at the Birchwood Hotel - included at no cost during your time with us! So, don’t wait - book your time in Paradise today!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.

Paradise by Seaside Vacations & Sales

Chincoteague, Virginia, United States

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$319.85

Waterfront Duplex with Stunning Assateague Island & Lighthouse ViewsbrbrExperience breathtaking water views from this charming waterfront duplex, featuring some of the best sights of Assateague Island and the iconic Lighthouse. The property includes a brand-new floating dock with a designated slip on deep water, perfect for boating enthusiasts. Spend your afternoons fishing or crabbing from the shared pier, or enjoy the small sandy beach area, accessible during low tides.brbrThe first-floor screened porch spans the entire level, offering panoramic water views and a relaxing space to unwind. Inside, the main level features a spacious open floor plan with a fully stocked kitchen, living room with great views, and a large dining table where the whole family can enjoy meals together. The first-floor den includes a king and twin bed with a private full bathroom, providing comfortable accommodations for guests.brbrUpstairs, two additional bedrooms share a hall bath. The rear bedroom has two twin beds, while the front bedroom offers a full bed, a twin sleeper, and private access to a second screened porch. A winding creek, accessible from the pier, is perfect for catching your own minnows or simply enjoying the serene surroundings.brbrThis waterfront retreat combines relaxation, recreation, and incredible scenery for a memorable stay.

Beechnut Villa- Waterfront with Lighthouse Views, Floating Dock & Deep Water Boat Slip

Chincoteague, Virginia, United States

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$309.03

Total Gem!! Historic Chincoteague Island home totally refurbished for comfortable island living. 3 bedrooms, 2.5 bathrooms, kitchen with granite countertops and stainless-steel appliances. Pet friendly, sleeps 8 and located off of East Side Road on Pointer Lane and boasts an acre of land. Peeks of Assateague Island and the channel are found from the yard and upper levels. Public boat launch nearby (decals for boat launch area at town office) so plenty of room for the boat or launch a kayak. Large dining area, laundry room with nice size washer/dryer and front porch. This is a great home for enjoyable island living. Dog only, 2 dog limit. $ 75 non-refundable pet fee. Kitchen also has a blender, Keurig coffee Maker and a regular coffee maker. Outside Charcoal Grill and outside picnic TablebrbrCancellations 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: 1K,2Q, F Sleep Sofa. Linens and Towels are not provided brbrSunday Change Overbrbr2026 Prime Season $ 300 per night $ 2100 week br2026 Off Season $ 200 per night $ 1400 week with 3 night minimumbr brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Endless Summer - Spacious 3BR, 2 Bath home w/large yard. Pets allowed.

Chincoteague, Virginia, United States

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$251.52

2BR/2.5B***(2Q,1D S/S) Amenities: Central A/C, W/D, WiFi, Microwave, TV- ROKU, Screen Porch, Dishwasher, Boat Dock. Beach chairs, boogie board and soft cooler provided for your use. brbrDeep Water town home with private dock on Assateague Channel. Tern Inn is totally remodeled for your stay. Within walking distance to Memorial Park, boat rentals and restaurants. Balconies on both levels and a deep water dock. Come enjoy!. Providing linens and towels this year. Beach chairs, boogie boards and soft cooler provided. NO PETS AND NO SMOKING. LINENS AND TOWELS PROVIDEDbrbrPLEASE NOTE IF BRINGING A BOAT PLEASE CONTACT OUR OFFICE TO VERIFY THAT THE BOAT WILL FIT IN THE SLIP. brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrBed Sizes: 2Q ,1D S/SbrbrSunday Change Overbrbr2026 Prime Season Rate $ 1477 per week/ weekly rental prime season only br2026 Off Season Rate $ 1078 per week / $ 154 per night with 3 night minimum brbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Tern Inn - Water Front - Townhouse, deep water dock. LINENS AND TOWELS,

Chincoteague, Virginia, United States

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Sleeps

$301.94

Named for Chincoteague’s iconic wild ponies, this fully renovated 2BR/2BA vacation home sleeps 8 and is ideal for families and groups. Features include a spacious upstairs den (queen, twin, futon), modern kitchen, fast WiFi, and open living areas. Enjoy a clean, comfortable stay close to dining, shops, galleries, parks, and island attractions. Perfect for relaxing, biking, and exploring—book your Chincoteague getaway today!brbrbrWhat this place offers:brbrUnique in that linens and towels are provided for no extra charge!brBathroombrIroning board and ironbrBathtubbrHair dryerbrCleaning productsbrShampoobrConditionerbrBody soapbrOutdoor showerbrHot waterbrBedroom and laundrybrFree washer – In buildingbrFree dryer – In buildingbrEssentialsbrHangersbrRoom-darkening shadesbrHandheld Garment steamer and mini ironbrClothing storage: closetbrbrEntertainment:br58” and 32” HDTVs with Roku and 43 Amazon Fire TV,brBooks, jigsaw puzzles, and specialty board games like Air PictionarybrbrHeating and cooling:brCentral air conditioningbrWindow AC unitbrCeiling fansbrPortable fansbrCentral heatingbrbrHome safety:brSmoke alarmbrCarbon monoxide alarmbrFire extinguisherbrFirst aid kitbrNight lights in every roombrInternet and officebrWi-FibrDedicated workspace in a common spacebrbrKitchen and dining:brKitchenbrSpace where guests can cook their own mealsbrRefrigeratorbrMicrowavebrCooking basicsbrPots and pans, oil, salt and pepper, Italian Seasoning, RosemarybrDishes and silverwarebrBowls, plates, cups, etc.brFreezerbrDishwasherbrStovebrOvenbrHot water kettlebrCoffee maker: drip coffee maker, pour-over coffeebrWine glassesbrToasterbrDining table with 6 chairsbrbrLocation features:brPrivate entrancebrSeparate street and building entrancebrOutdoorbrPrivate backyard – Not fully fencedbrAn open space on the property usually covered in grassbrOutdoor furniturebrOutdoor dining areabrPortable green BBQ smoker /grill: charcoalbrBeach essentialsbrBeach towels, beach blanketbrbrParking and facilities:brFree driveway parking for 3 cars on premisesbrFree street parking on East side of Clark StreetbrbrServices:brSelf check-inbrKeypadbrCheck yourself into the home with a door codebrLong term stays allowedbrAllow stay for 28 days or morebrbrBEDROOMS:brBedroom 1- 1 Queen BedbrBedroom 2- 1 Queen BedbrBedroom 3 / Den- 1 Queen Bed, 1 Twin Bed, Futon Bed (second level)brbrINDOOR FEATURES: Central Air Conditioning/Heat, 2 Smart Roku TVs and 1 Smart Amazon Fire TV, Office Space, Kitchen Utensils/Dinnerware, Protective Mattress and Pillow Covers, Unique Themed Bedrooms to fit your preferences.brbrOUTDOOR FEATURES: Outdoor Shower, Screened-in Front Porch with Swing, table and chairs, Portable Green Charcoal Smoker/Grill, Outdoor Patio and Dining Area, Private Parking for 3, Keypad Lock, 4 Mountain BikesbrbrbrbrbrbrBONUS FEATURES:brEssential Oil DiffuserbrRemote controlled LED candlesbrTwo bikes with locks and a bike pump. Please note: you will need to bring your own helmets. Additionally please follow all posted safety signs and follow road rules. By using our bikes you assume all responsibility and liability for your safety.brbrGuest accessbrYou'll have the entire house to yourself plus a beautiful patio.brOther things to notebrPlease specify which beds you will be using.br-We use a professional cleaning company for your safety. There will be a cleaning fee added to your bill.br-8 guest max includes use of the sofa bed by 1 guest. NO unregistered guests.br-Access into home is by stairs only (3-4 steps).br-4 adult sized bikes are provided for your use. If you prefer to ride with a bike helmet, please bring your own properly fitting helmet as they will not be provided. Please ride responsibly and adhere to all posted signs. By using our bikes you assume all responsibility and liability for your own safety.

The Neigh-Neigh - Location! Location! Location!

Chincoteague, Virginia, United States

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$581.62

If you're looking for a spacious vacation home suitable for ALL of your friends and family members, My Happy Place will give you all you need and MORE! You'll enjoy almost 3,000 sq ft of beautiful beachy interior with a SUPER BONUS attached 2 car garage set up with a 70 TV and seating for all. There are two decks in the super private and quiet backyard that offers a private above ground pool and a large shed filled with guest bikes for your enjoyment. You can use the kayaks and the SUP if you'd like to enjoy a paddle from the near by launch on the east side of the island where you can enjoy upfront views of the incredible lighthouse and the amazing wild Chincoteague Ponies. Located on a quiet street just off Ridge Road and centrally located on our favorite island, My Happy Place is a super short drive to the Chincoteague National Refuge and the beautiful beaches of Assateague Island. As seasoned hosts, we pride ourselves in providing more for our guests than you'll ever find at any other vacation rental on the island. This is a Saturday to Saturday 7 day minimum rental during the peak season. 3 day minimum otherwise.brbrExperience the magic of Chincoteague at our beloved home and make it YOUR HAPPY PLACE too!

My Happy Place : Space for EVERYONE plus a PRIVATE POOL too!

Chincoteague, Virginia, United States

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Sleeps

$354.49

Life’s at ease with a bay breeze…..brbrDo you yearn to be so close to the water that you can take in that salty, sweet sea breeze while you sleep Imagine fishing and crabbing only steps from your house - or having your Boat docked just behind the house - all the joys of living at the Water’s Edge.brbrWelcome to Water’s Edge in the heart of Chincoteague Island - this home delivers, y’all! Not far from Downtown Main Street, you’ll feel a million miles away, yet be so close to everywhere you want to be! A Townhome with all the comforts of home - and then some!brbrYou’ll love relaxing in the Living Area - sink into the huge Sectional and take in amazing Views of the Chincoteague Bay. We should mention this lovely Townhome directly faces the most gorgeous Sunsets - and there’s nothing like a Chincoteague Sunset. Enjoy Free WiFi and Flat Screen Streaming Only TV, and simply hang out with those that matter most. (Fireplace is decorative only). You may not even turn on the TV once you see the Views from the Waterfront Decks - and there are multiple Decks with all sorts of fabulous Views!brbrJust off the Living Area, follow the gorgeous Hardwood Floors to the Kitchen and Dining Area. The Chef in your family will appreciate how well-stocked it is! Not one to cook on Vacation No worries - there are many options just a hop, skip, and jump away. Dine in the comfort of Central AC, or wander out to the Deck off the Kitchen, which has a Dining Table and welcomed shade. This is a great spot when the wind is blowing, but you still long to sit outside. Just off the Living Area and Kitchen, you’ll find a convenient Half Bath. brbrWater’s Edge sleeps 5 in pure comfort. Wandering upstairs, you’ll find 2 Bedrooms and 2 Full Baths. Bedroom 1 is a Master and has a luxurious King Bed and magnificent Bay Views from your Private Deck. Just imagine slipping out to stargaze while the rest of the family slumbers. There is also Flat Screen Streaming TV, and a Private Master Bath with Tub/Shower Combo and Double Vanity. brbrJust down the Hall, Bedroom 2 sleeps 3 with a Queen Bed and a Twin Bed, and also has a Flat Screen Streaming TV. This room also has its own Private Deck! A 2nd Full Bath is in the Hall and has a Walk-in Shower. There’s even a convenient 2nd Floor Laundry with a Full Size Washer and Dryer - you can’t get this at a Hotel or Cabana. brbrBut we all know a Vacation is all about the Experience - and Water’s Edge IS an Experience you’ll treasure with your family forever. And OH, the Outdoor Living! Only a few minutes from Assateague National Seashore, where our Wild Ponies roam free, you can have your cake and eat it, too! Spend the day on the Beach shell-combing and sunbathing - or fishing - or hang out at the house, where you can crab and fish right from the Dock! Rent a Kayak and explore the shallow waters near the house, or bring your Boat and use the Boat Slip provided at no additional cost! You will never hear “I’m bored” from the kids on this visit!brbrSo, if Mother Ocean is calling you to live at the Water’s Edge, we’ve got the perfect homebase for all of your Chincoteague Adventures!brbrNo Smoking/No Pets -Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements.

Water's Edge by Seaside Vacations & Sales

Chincoteague, Virginia, United States

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Bath

Sleeps

$384.68

When you need to check off ALL of the boxes, you'll find everything you’re looking for at Riptide's Retreat. brbrNamed after one of Chincoteague's most beloved wild ponies Riptide, we've got everything you need to enjoy a spectacular vacation filled with memories that will last a lifetime. brbrEvery morning you can enjoy a peaceful sunrise as you look out towards the beautiful refuge where you'll find the southern heard of the famous Chincoteague Ponies. You'll also have direct views of the Assateague Lighthouse and Little Beach where you can paddle over and enjoy a more private beach experience. brbrWe provide all the essentials PLUS bikes, kayaks, beach/fishing cart, Bogg beach bags, beach towels, crab pots/traps, and more. brbrCome and enjoy the most amazing views from our multiple decks that look out over the Chincoteague Channel and the southern end of Assateague Island. You'll have unobstructed views of the Assateague Lighthouse as well as Little Beach both just a short kayak paddle away. There's plenty of parking for you and your guests too.brbrWant to bring your boat We've got you covered. You'll have access to our BRAND NEW private DEEP water footing dock. Want to enjoy fresh crab for dinner Use our crab traps and enjoy the freshest seafood ever. brbrWe've even included an outdoor dining area with seating for 10. You'll have a propane grill for your favorite feasts and there's a great spot with a firepit so you can make all the smore's you want for dessert.brbrIf you're wondering where the famous pony swim takes place each July, it shouldn't surprise you that it takes place on PONY SWIM LANE. You'll have a FRONT ROW SEAT when you stay at Riptide's Retreat during that magical week in July. Literally there is NO OTHER vacation rental on the entire island of Chincoteague that will get you closer to the wild ponies on swim day. brbrBut the BEST PART OF Riptide's Retreat is that you don't have to be there during Pony Penning week in July to see the ponies because they roam year round as they graze in their natural environment just across the channel on the Chincoteague National Wildlife Refuge. If you want an up-close personal experience, you can paddle over with our kayaks or jump in your boat for a super quick ride. brbrBy the way, the reason our home is called Riptide's Retreat is that Riptide is one of the most recognizable ponies in the southern herd and we're confident that you will likely see him and his band of beautiful mares during your stay. His dark chestnut coat contrasted by his beautiful blond mane makes him the Fabio of all ponies. I'll bet you will spot him during your visit. brbrAs the owners of four vacation rentals on Chincoteague Island, this one packs the most punch and definitely has that WOW factor for guests as they arrive and gaze out at the water and Assateague Island.brbrWe can't wait to see you come and enjoy.brbrOur home is pet friendly. Inquire with the host regarding limitations. This is a Sunday to Sunday rental during the peak season June - Mid September

Riptide’s Crossing: A waterfront getaway w/deep water dock and incredible views

Chincoteague, Virginia, United States

Bed

Bath

8

Sleeps

$492.25

5 BDRM, 3 FULL BATH, 2400SF, HOME ON 0.5 ACRE PRIVATE LOT WITH AWESOME WATERFRONT VIEWS FROM ANY FRONT HOUSE VIEW. NICE HARDWOOD FLOORS THROUGHOUT, SCREENED PORCH, 2ND FLOOR DECK AND LARGE EAT-IN KITCHEN ADD TO THIS SPACIOUS HOME. 2ND FLOOR WASHER/DRYER, STOVE, FRIDGE, DISHWASHER, CENTRAL HEAT-A/C AND CABLE / WIRELESS INTERNET READY MAKE THIS HOME EASY LIVING. FULLY FURNISHED (CAN VACATE FURNISHINGS IF NEEDED) ALL CLOSE TO SHOPPING, BEACHES, ACTIVITIES AND RESTAURANTS / COFFEEHOUSES. PETS CONSIDERED.

Stately Home on Chincoteague Island - Professionally Sanitized

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$201.11

Amenities: Central A/C,Microwave, Dishwasher, W/D, WiFi, TV w/Roku (bring your own login info) Sun Porch, Back Yard, Outside Shower, Two Parking Spaces and Off Street Parking Available.brbrSpacious in town home will sleep the whole gang. Walking distance to town and Maddox Blvd. This centrally location is the best. Three bedrooms and huge loft upstairs. Also offering a separate dining area and nice back yard.brbrTHIS HOME DOES NOT PROVIDE LINENS OR TOWELS. PLEASE BRING YOUR OWN OR CALL US TO RENT THEM.brbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less, then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge, and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrBed Sizes: 1 King, 1 Queen, 2 Doubles, 4 Twins w/Trundles. brbrSaturday Change Overbrbr2026 Prime Season Rates $ 1253 per week br2026 Prime Out Rates $ 1001 per week / $ 143 per night 3 night minimumbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

My 3 Buoys - 3BR home, close to town . 2 first level BR's. NO LINENS PROVIDED

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$280.59

3BR/2B***(Single Level Home) {2Q, 1Bunk w/2T} Amenities: Central A/C, Microwave, Cable, WiFi, W/D, Screen Porch, Deck, Barbeque Grill, Outside Shower, Handicap Accessible with a ramp and handicap shower. A $75.00 pet fee per dog will be added. brbrAmenities: Central A/C, Microwave, Cable, WiFi, W/D, Screen Porch, Deck, Gas Grill, Outside Shower, Handicap Accessible with a ramp and handicap shower.brbrShuckers Tump is a pet friendly home, located in town within walking distance to shops and restaurants. Handicap Accessible with a ramp and handicap shower. Formerly known as Cowboy Cottage. This home is open and bright with easy access to all island attractions. brbrThis Property accepts Dogs Only (limit 2)brLINENS AND TOWELS PROVIDEDbrbrCancellations 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).brBed Sizes: 2 Queens, 1 Bunk Bed w/2 TwinsbrbrSunday Change Overbrbr2026 Prime Season Rate $ 1505 per week / $ 215 per night ( 3 night minimum)br2026 Off Season Rate $ 903 per week / $ 129 per night (3 nights minimum) brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Shucker's Tump - pet friendly, Lg screened porch. LINENS AND TOWELS PROVIDED

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$168.44

Traveling - it leaves you speechless, then turns you into a Storyteller. Welcome to the Chincoteague Island Retreat you've been longing for - tucked away on a quiet lane in the heart of our tiny Island. George's Retreat is in the perfect location, just off of Maddox Boulevard, aka the Beach Road - you can walk or ride your bike to many, Restaurants, Shops, and Activities up and down the Boulevard, and the Beach is a short bike ride away. This delightful Duplex sleeps 6 with all the comforts of home and then some. And driving down the sleepy dirt road to the Cottage, you will know right away you won't be disturbed by the hustle and bustle of the busy season. brbrbrbrGeorge's Retreat is just perfect for a family or even several couples traveling together. As you enter, you'll love the modern Coastal Decor, welcoming colors of Sand and Sea, and comfortable furnishings. The Living Area has plenty of room for all, and is a great place to relax with Flat Screen Cable TV and Free WiFi after a fun-filled day at Assateague National Seashore. The well-equipped Kitchen has everything you need to make mealtime super easy, and with the double sided Breakfast Bar and Table, there's room for all. Whether grilling the Fresh Catch of the Day or steaming some Local Crabs, the Screened Porch is an awesome place to dine Al Fresco and take in salty, sweet sea breezes. There's even a fabulous Enclosed Outdoor Shower with hot and cold water - always a treat after a sandy beach day!brbrDown the Hall, you'll find 2 Bedrooms and a Full Bath with Tub/Shower Combo. Bedroom 1 has a comfy Queen Bed with soothing colors of Sea Glass. Across the Hall, Bedroom 2 has 2 Twins and a fun Nautical Flair.There is also a Full Size Washer and Dryer in the downstairs Full Bath. Wander upstairs, and you'll love the spacious Master Suite with Queen Bed and Sitting Area - perfect for those wanting a bit more privacy. The Master Bath has a Tub/Shower Combo and tons of space - just lovely! brbrWhether visiting Chincoteague Island for our famous Wild Ponies, Shell Combing, or just some Fun in the Sun, Budget-Friendly George's Retreat really can't be beat - Book your time in Paradise today!brbrGeorge's Retreat - You don't have to be rich to travel well!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. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.

3 bedroom home near Maddox Blvd by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$182.46

Sometimes you just have to go with the waves….. brbrLooking to catch a beach getaway at a family-friendly price Then look no further than Fishhook Hideaway on Deep Hole Road - truly the catch-of-the-day! This adorable 2 Bedroom/2 Full Bath home is located in the heart of our little Island - just a short stroll from Maddox Boulevard, Steamers, and The Island Creamery, and a very short 5 minute ride to Assateague National Seashore!brbrFishhook Hideaway has all you need for the perfect family getaway. You’ll love relaxing in the comfort of Central AC after a fun-filled day at the Beach, and enjoying Free WiFi and Flat Screen TV. Newly renovated and with brand new furnishings, it’s comfy and cozy. Just off the Living Area, you’ll find a Full Bath with Tub/Shower Combo, and a Full Size Washer and Dryer for your convenience. Wander up just 3 steps, and you’ll find the Well-stocked Kitchen supplied with all you need to make mealtime a bay breeze. No need to dine out every day - unless you want to!brbrThis adorable Townhome sleeps 7 in comfort and style. Wandering upstairs you’ll find 2 beautifully decorated Bedrooms and a Full Bath. Bedroom 1 has a comfy King and is adorned in Colors of Sand and Sea. Bedroom 2 sleeps 5 with a Pyramid Bunk (Twin over Full) and a Full Bed - just perfect for the kids!brbrDon’t wait - book your island time today at Fishhook Hideaway - don’t let this be the one that got away! We just know you’ll be hooked!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.

Budget friendly Chincoteague townhome by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Bed

Bath

6

Sleeps

$506.24