Home Vacation Rentals By Owner In Chincoteague, VA

Showing 200 Of 262 Vacation Rentals
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Exceptional(1)

$256.1

/ Nightly
Private Vacation Home

The View-Waterfront w/ Shared Crabbing Pier

Chincoteague, Virginia, United States

Newly Renovated Waterfront Property with breathtaking views of the brAssateague Lighthouse and Assateague Island. The Assateague Channel is teeming with waterfowl and wildlife, making this a true birdwatchers paradise. Enjoy spectacular sunrises and sunsets from three private balconies.brbrThe brand-new kitchen features warm tones and modern finishes, counter seating, new appliances with ice maker, a filtered water system at the faucet, and updated flooring throughout main level. A freshly painted interior and a new dining area seating six create a bright, welcoming space for meals and gathering. New central air and heating.brbrWide new sliding glass doors open to spacious waterfront balconies, extending indoor-outdoor living. Thoughtfully chosen natural coastal finishes reflect the surrounding water and marsh, bringing the serenity of the outdoors inside.brbrA rear den with a queen sleeper, new half bath, and workspace offers a third semi-private sleeping area and opens to a third private deck with a new large gas grill.brbrUpstairs, you will find two inviting bedrooms, each with its own private bathroom. The waterfront king suite offers sweeping views and a private waterfront balcony, perfect for morning coffee or quiet relaxation. The second bedroom features a queen bed and a king trundle bed, providing flexible sleeping arrangements for families or friends.brbrFor outdoor enjoyment, the property features an extra large outdoor shower and access to three shared piers, perfect for crabbing and taking in the peaceful surroundings. A designated community kayak launch pad is available.
Bed 2

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Bath 1

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Sleep 6

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Exceptional(2)

$581.28

/ Nightly
Private Vacation Home

Osprey Nest- Waterfront on Chincoteague Bay w/ Pier

Chincoteague, Virginia, United States

A comfortably appointed coastal retreat perched on the tranquil edge of Chincoteague Bay.brbrSet in one of the island’s most peaceful waterfront locations, Osprey Nest offers sweeping, unobstructed views of the bay, salt marsh, and abundant wildlife. Watch herons glide over the water, ospreys returning to their nests, and fishing boats making their slow morning passes—all from the comfort of your home. The property sits just minutes from Chincoteague’s charming shops and restaurants, and a short drive from the wild beaches and famed ponies of Assateague Island.brbrDesigned with an inverted floor plan to showcase the scenery, the home’s upper-level features panoramic windows that bring the outdoors in, along with an open kitchen, dining area, living room, and half bath. Sunlight, sky, and water surround you from every angle.brbrDownstairs, the two waterfront queen bedrooms each include their own private balcony—perfect for lingering over morning coffee or savoring sunsets that paint the bay in gold. Two additional bedrooms feature twin beds. All four bedrooms offer full private baths, providing comfort and privacy for every guest.brbrA large, screened porch offers shaded breezes and views of the marsh, while the shared dock invites crabbing, fishing, birdwatching, or quietly taking in the shifting tides and spectacular evening colors.brbrOsprey Nest is a peaceful sanctuary with some of the best views on the bay—an ideal place to unwind, explore, and experience the natural beauty of Chincoteague.
Bed 4

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Bath 1

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Sleep 10

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Exceptional(11)

$292.65

/ Nightly
Private Vacation Home

Crepe Myrtle Cottage by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Give me the Sea and a little Cottage just to be…. brbrThe first time we saw ‘Crepe Myrtle Cottage’, we felt an inviting warmth pulling us in. Very difficult to describe, it’s the feeling of true Southern Charm, mixed with the appeal of modern amenities and chic decor. To us, it is the absolutely perfect combination of the quintessential Chincoteague Cottage and all that is shiny and new - at the same time.brbrCrepe Myrtle Cottage is easily spotted as you drive down Church Street, in the very heart of our beautiful little island. In the front yard, a wise and wonderful Crepe Myrtle Tree welcomes you with its winding and unique branches. This circa 1930’s home has been completely renovated - you are in for quite a surprise.brbrUpon entering, the cozy Front Porch lining the cottage is so alluring. Whether curling up with a good book, or sharing stories of the day’s adventures, you already know you’ll be spending lots of time here. You’ll love relaxing in the Living Area with its warm Hardwood Floors and Trim - special touches of yesteryear - and enjoying Free WiFi and Flat Screen Cable TV. Follow the French Doors to the Dining Area with plenty of seating for all at the huge Dining Table. The gorgeous and unique Chandelier sets a wonderful mood for the room. brbrThe Chef in your family will love the brand new Kitchen - gleaming granite, stainless appliances, stunning backsplash - meal prep will feel like anything but a chore. Dine indoors or Al-Fresco on the back Deck. Just off the Kitchen is the Laundry Room and a Full Bath with Tub/Shower Combo.brbrCrepe Myrtle Cottage sleeps 8 more than comfortably in 3 Bedrooms. On the 1st floor, Bedroom 1 has a comfy Queen Bed.. Down the Hall, Bedroom 2 has a King Bed, Flat Screen TV, and classic good looks. A 2nd Full Bath with Tub/Shower Combo is located between the 2 Bedrooms, convenient to the Living Area. Just off the Kitchen, wander upstairs to find enormous Bedroom 3. Stairs in these classic Chincoteague Homes can be narrow, so this may not be a great place for the littlest ones, but is amazing for older kids and adults. This oversized room has a Full Bed and 3 Twins, as well as a cozy reading nook. There is not 1, but 2 more Flat Screen TVs in this space, as well. brbrYou’ll love the Outdoor Living at Crepe Myrtle Cottage, as well! The large, lush backyard is fenced in, creating a very private hangout. There’s an inviting hammock for an afternoon siesta, and an Outdoor Shower for rinsing off after a day at the beach. And you can grill the fresh catch of the day while listening to the tree frogs sing. Does it get any better than this !brbrCrepe Myrtle Cottage - of all the paths you take in life, make sure a few of them are sandy….brbrSeaside Vacations does not rent 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.
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Bath 2

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Sleep 8

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$336.9

/ Nightly
Private Vacation Home

Chincoteague Island House Sir Whelk-A-Lot Kayaks Included! Downtown Location!

Chincoteague, Virginia, United States

We WHELK-come you and your family to come stay at our unique island vacation home. The idyllic island of Chincoteague offers an array of vacation experiences, and we are located in the heart of it all! Use our kayaks and boogie boards by day, and take advantage of our convenient proximity to downtown by night. Our family fell in love with this slice of paradise many years ago, and we want to give you and your family the opportunity to experience all its beauty with the best stay possible.brbrbr~ABOUT THE HOUSE~brThis is a 3 bedroom, 2 bathroom, 1221 sq. ft. beach house located in town. We have a full kitchen, living room, dining area, office space, and screened-in porch. This house is perfect for a large family or two small families. We comfortably sleep 8 but can sleep a maximum of 10 with use of our sofa bed. Our second floor includes an additional small living space with a Smart TV and an attached bathroom. Our kayaks, beach supplies, and grill are available for use with NO additional fees. Please note, LINENS AND TOWELS ARE NOT INCLUDED but can be rented for a fee.brbrHIGHLIGHTS: Proximity to Beach, Free Wi-Fi, Outdoor Shower, 4 Kayaks (10’ 3”), Porch Swing, Basic Beach Supplies, Charcoal Grill, In-Unit Laundry, *NO ADDITIONAL FEES FOR USE OF OUR AMENITIESbrbrBEDROOMS: Bedroom 1- 1 Queen Bed | Bedroom 2- 1 Bunk Bed | Bedroom 3- 1 Queen Bed, 2 Twin Beds (second level) | *Sofa Bed in living roombrbrINDOOR FEATURES: Central Air Conditioning/Heat, Smart TV, Roku, Office Space, Kitchen Utensils/Dinnerware, Protective Mattress and Pillow Covers, Unique DecorbrbrOUTDOOR FEATURES: Outdoor Shower, Screened-in Front Porch with Swing, Charcoal Grill, Outdoor Dining Area, Clothing Line, Private Parking for 1, Keypad Lockbrbrbr~IMPORTANT INFORMATION~ brLINENS AND TOWELS ARE NOT INCLUDED. However, we can provide these items for you at a cost of $17 per bed. This is to keep our cleaning and booking fees down as laundering services are costly on the island. | We use a professional cleaning company for your safety. There will be a cleaning fee added to your bill. | Access into home is by stairs only (3-4 steps). | The steps to the second level are narrow. | 4 kayaks are provided. We supply 4 keyhole life jackets (standard orange) but feel free to bring your own properly fitting life jackets. Guests will need a way to transport kayaks. | Our personal beach gear and bikes are available for your use but these items are not professionally maintained. For this reason we can not guarantee all items will be in usable condition.brbrbr~ABOUT THE LOCATION~brOne of the highlights of our beach house is that it is within walking distance to the Historic Downtown of Chincoteague! Here you will find restaurants, art galleries, gift shops, coffee shops, the waterfront park, a fishing pier and all that Main St has to offer! We are located off of the intersection of Clark St and Main St. Three blocks north you will find Chincoteague's other main road, Maddox Blvd, which will take you right out to the beach!brbrGetting around is extremely convenient from our location. Our close proximity to downtown eliminates any parking hassles! In addition to being within walking distance to Chincoteague's in-town activities, any part of the island is just a bike ride away! We have parking for one dedicated to our building and free street parking facing east on Clark St.brbrbr~HOUSE POLICIES~ brNo smoking/vaping in house or on porch / No pets / No parties/events / Quiet hours are 10pm-7am / No loud music / No undeclared guests / Report damage / No stealing / No illegal substances on premises / Follow all rules regarding amenities (ex: relock bikes, no manipulation of TV cables, follow kayak safety and permit regulations etc.) / Follow all checkout instructions (*you may be billed if additional cleaning is required) / Failure to follow these rules may result in loss of security deposit, added fees and/or eviction
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Bath 2

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Sleep 8

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Exceptional(4)

$618.1

/ Nightly
Private Vacation Home

Sunset in Sunnywood: A peaceful retreat with a PRIVATE POOL!

Chincoteague, Virginia, United States

Nestled away on a serene and private lot in the sought-after Sunnywood neighborhood, this beloved vacation home will make you forget the stresses of life and help transition you and your guests into vacation mode on our favorite little island on the Eastern Shore of Virginia. Brand new to the vacation rental market and owned by highly rated hosts, this home is the very best of their portfolio of properties on Chincoteague.brbrInside you'll find all the amenities and more for you and all of your guests. Take a look at the pictures and fall in love. The first floor master bedroom is super-sized and includes a reclining couch and huge smart TV. Two regular sized bedrooms can each sleep up to 4 and there's PLENTY of closet space for everyone. The upstairs family suite consists of a HUGE master bedroom with a reclining loveseat, wall of closets and a large smart TV. But wait, there's more: The adjacent living area features an entire room providing additional living space as well as more sleeping options. There's an extra large master bathroom has double vanities and a walk-in closet. brbrLocated just one block from Veterans Memorial Park, you'll be just moments away from launching your boat or casting a line. There's a dedicated kayak launch and a playground for the young at heart too! Back at the house, there's plenty of parking for everyone, your boat and even your RV.brbrThe quintessential front porch complete with a row of rocking chairs is the perfect place to catch the beautiful colors of the evening sunsets. The large side yard will give you all the space you need for outdoor fun. An above ground pool (24' x 52) will be ready for your enjoyment in the peak season from Memorial Day to Labor Day. Here's the big bonus: The super sized outbuilding is getting a pool house style makeover this winter and will provide yet another place for guests to relax and enjoy. brbrThe hosts provide a variety of bikes, beach equipment and crabbing supplies for use during your stay. brbrThis home comes with a personalized vacation guide so you can plan every moment of your stay. And once you arrive, you can opt in for updated event information specific to your reservation timeframe. It's like having a vacation concierge at your fingertips. Please note: This is a SUNDAY to SUNDAY rental during peak season mid May to Early September.brbrLinen package is available based on head count. If selected, Bed linens and bath towels will be provided prior to arrival. Inquire when you make your reservation. We are always happy to answer any questions you may have. 973-479-7534
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Bath 3

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Sleep 18

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Exceptional(4)

$315.02

/ Nightly
Private Vacation Home

Starbright Cottage by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Reach for the Stars on your next Chincoteague Island Vacation…..brbrWelcome to whimsical Starbright Cottage on beautiful Chincoteague Island! This adorable 4 Bedroom home is not only in an amazing mid-Island location, it welcomes your whole family - including your friendly Dog! brbrStarbright Cottage has the allure of a bygone era, combined with the modern Amenities you want and need. Perched at the corner of Chicken City Road and Church Street, you’re in the perfect location for all of your Island adventures. Walk or ride your bike to Shops, Dining, and even the Beach. With a spacious lot and Fenced-in Yard, it's a wonderful place for both the human and the furry members of your family. And there's plenty of room to park your Boat and other Water Toys!brbrAs you enter Starbright Cottage, the first thing you notice is the large Screened Porch that lines the front of the home. You can already see yourself curled up with a good book, or maybe enjoying your morning coffee as you watch the bicyclists go by. Starbright Cottage is one of those homes that has so many nooks and crannies - the open layout is just right for spending time with those who matter most, without ever feeling crowded. brbrYou’ll love relaxing in the Sunroom with vibrant Colors of Sea Glass - a great place to share stories of the day’s adventures, or maybe some family movie time in the comfy Living Area with Flat Screen TV and Free WiFi. This eclectic circa 1950’s home has quite a history, and at one point was even an Art Gallery. The Living Area is comfortably furnished, and adorned in Rich Reds, Exposed Beam Ceilings, and fun pops of cheerful colors. There’s even a cozy Electric Fireplace for those chilly off-season stays - one of our favorite times at the Beach!brbrJust off the Living Area, you’ll find the Kitchen and Dining Area. The Chef in your family will love how well-stocked the Kitchen is, and with multiple Dining Areas, you can change it up at every meal! Dine in the Eat-in Kitchen, Dining Area, Screened Porch out front, or Al-Fresco in the Backyard while your furbaby lounges in the sunshine. brbrStarbright Cottage sleeps 9 more than comfortably in 4 Bedrooms. Bedrooms 1 and 2 are on the 1st Floor, perfect for those not wanting to deal with stairs, and both have a comfy Queen Bed, The Full Bath on this floor has a Handicap Accessible Shower with removable showerhead. Wandering upstairs, you’ll find 2 more Bedrooms, plus a Common Area with a Full Futon. Engulfed with welcoming warm wood and vibrant colors, the upstairs area sleep 5. Bedroom 3 has a Full Bed, while Bedroom 4 has 2 Twins, as well as a Flat Screen TV. The upstairs Full Bath has a Walk-in Shower. A Futon in the Common Area is perfect for additional sleeping space, or grab a book off the shelf and get lost in it for a while. brbrWhether you enjoy lounging on the Beach or searching for our famous Wild Ponies, Starbright Cottage is an amazing, affordable, and family friendly home that is the perfect homebase for your Island adventures! What are you waiting for - grab the kids, the dog, and maybe even your Mother-in-Law and make your way to Chincoteague today!brbr**FLEX-STAY HOME**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 per Dog. Dogs MUST be current on Flea/Tick Preventative & Immunizations. No Cats. brbrEvery effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
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Bath 2

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Sleep 9

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Exceptional(23)

$190.53

/ Nightly
Private Vacation Home

Eel Creek Escape - Water Front - Water Access - Screened Porch NO LINENS

Chincoteague, Virginia, United States

Amenities: New for 2024 WIFI and 65 Smart TV. Central A/C, W/D, Microwave, Dishwasher, TV, DVD, Screened Porch, Outside Shower & 2 decksbrbrBring your kayaks and kids! This is a bright tastefully decorated rancher! Nice crabbing dock for great sunrises. Garage has been converted into a separate living space with a TV and couch, perfect for the teenagers. Located in a quiet neighborhood and in walking distance of restaurants and attractions. All bedrooms on the same level. Gas fire pit. NOW HAS INTERNET AND SMART TV. br brNO LINENS AND TOWELS PROVIDED SO BRING YOUR OWN OR CALL US TO RENT THEM.brbrCancellations made 30 days prior to arrival will receive 100% of refund  of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid.  If less then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrBed Sizes: 1 Queen, 1 Double, 2 Twins, 2 Queen Sleep SofabrbrSunday Change Overbrbr2026 Prime Season Rates $ 1498 per week / $ 214 per night with 3 night minimumbr2026 Off Season Rates $ 952 per week / $ 136 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. ****
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Sleep 8

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Exceptional(28)

$184.67

/ Nightly
Private Vacation Home

Misty Manor - 3BR home, sc. porch & NO PETS. NO LINENS PROVIDED

Chincoteague, Virginia, United States

Amenities: Central A/C, W/D, Dishwasher, Microwave, 2 TVs, WiFi, DVD, Screened Porch, NO PETS ALLOWED. brbrThis bright and cheerful home is tucked away on a private lane next to the historic Misty's Pony Farm. With a quiet location and a spacious screened back porch, this house is perfect if you want to relax in nature but still be close to downtown. It offers a first floor bedroom and bath. Close to Summer Memories. Now offering WiFi.brbr THIS 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 Queen, 1 Double, 2 Twin, 1 FutonbrbrSunday Change Overbrbr2026 Prime Season Rate $ 1106 per week br2026 Off Season Rate $ 903 per week/ $ 129 per night brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****
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Bath 2

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Sleep 8

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Exceptional(27)

$229.09

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Private Vacation Home

Creekside Paradise - Water front &Access -Pet Friendly -Shared Dock NO LINENS

Chincoteague, Virginia, United States

Amenities: Central A/C, Dishwasher, TV w/Chromecast only (no cable), DVD, WiFi, W/D, Microwave, Jacuzzi Tub, Deck, 2 Screen Porches, 1 Kayak w/life preserver, Bikes(2 adult) , Shared Dock.brbrThe unobstructed view of Eel Creek and Little Oyster Bay will get your attention at sunrise and sunset! Put your kayak in the water at the shared dock at high tide. WiFi available. George Foreman Outdoor Electric Grill. New laminate flooring installed downstairs. Community Boat Dock.. Cancellations 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).brbrPet friendly home $75.00 (per pet) fee will be added to your reservation. Ring security camera at entrance door. NOTE: All vehicles included electric rented vehicles must be parked in a parking space or overflow parking no parking on grass or on waterside of property. LINENS AND TOWELS ARE NOT PROVIDED SO BRING YOUR OWN OR CALL US TO RENT THEM.brbrbrbrBed Sizes: 1 Queen, 1 Double, 1 Twin, 1 Double FutonbrbrSaturday Change Overbrbr2026 Prime Season Rate $ 1204 per week ($ 172 per night) Weekly Rental Only Prime Season br2026 Pony Swim Rate $ 1400 per week ( $ 200 per night) Weekly Rental Only Pony Swim br2026 Off Season Rates $ 1001 per week $ 143 per night 3 night minimum brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****
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Bath 2

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Sleep 7

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