Vacation Home Rentals By Owner In Chincoteague, VA

$378.73

Sanderling - Spacious 4BR home with fenced in back yard & dog friendly.

Chincoteague, Virginia, United States

Special: Book any remaining week in Prime Season for $ 2002 per week / $ 285 per night 7 night minimum4BR/2BA Amenities:1 K bed, 3D.Refrigerator, stove, m/w, toaster, w/d, WIFI, TV-Streaming, dw, decks, 2 dog kennels. Dogs Friendly Only ! No smoking ! brbrSpacious home on Chincoteague Island, will house the whole gang in comfort. Dog friendly home with fenced in back yard and two dog kennels. Walking distance to Maddox Blvd, shopping and Restaurants. Nice back deck and 5-minute drive to the beach.Well equipped kitchen with large dining table. DOG FRIENDLY ONLY ! NO SMOKING. brThere is an additional $ 75 per pet fee for any dog. br brPlease ask about our cancelation policy. 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). k, 3 Doubles.br brbrBed Sizes: 1K, 3DbrbrChange Over Saturday brbrSpecial: Book any remaining week in Prime Season for $ 2002 per week / $ 285 per night 3 night minimumbrbr2026 Prime Season Rate $2200 per week / $ 315 per night 3 night minimum br2026 Pony Swim Rate $ 2400 per week / $ 343 per night 7 night minimum br2026 Off Season Rate $ 2000 per week / $ 285 per night 3 night minimumbrbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Bed

Bath

Sleeps

$270.22

/ Nightly

Private Vacation Home

Shear Water - 3BR home, fenced in yard and pet friendly, NO LINENS PROVIDED

Chincoteague, Virginia, United States

Amenities: Central A/C, Dishwasher, W/D, DVD, Cable TV, WiFi, Deck, Large Fenced yard, Private Outside Rinse AreabrbrUnique Chincoteague home located in the heart of downtown. Close to Main Street, this property is within walking distance to shops, entertainment and restaurants. This pet friendly home has large fenced in back yard, perfect for your furry friends. Sandy from a long day at the beach No worries, this house has a private outside rinse area. br brTHIS HOUSE DOES NOT PROVIDE LINENS OR TOWELS. PLEASE BRING YOUOR 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).brbrbrBed Sizes: 1 King, 2 Twins, 1 Daybed with TrundlebrbrSaturday Change Overbrbr2026 Prime Season Rates : $ 1603 per week / $ 229 per nightbr2026 Off Season Rates: $ 1360 per week / $ 195 per night (3 Night Minimum)brbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Bed

Bath

Sleeps

$200.5

/ Nightly

Private Vacation Home

‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!

Chincoteague, Virginia, United States

Escape to coastal paradise with this charming vacation rental in Chincoteague Island, VA. Spend your getaway with our Chincoteague Ponies — or bring your own! Offering a barn with stalls and a horse pasture with a run-in, this spacious 2-bedroom, 2-bath home is the perfect retreat for avid riders. Witness a sunset on the beach, explore Chincoteague National Wildlife Refuge and Assateague Island, or simply cozy up by the fireplace. Don't miss out on this gem for your visit to the Eastern Shore!brbr-- THE PROPERTY --brbrHorse-Friendly Property | brBedroom 1: King Bed | Bedroom 2: Queen Bed | Sunroom: Sleeper Sofa | Living Room: Sleeper Sofa brbrINDOOR LIVING: Smart TV, board games, books, fireplace, group-friendly dining table, sunroombrOUTDOOR LIVING: 2 12x12 horse stalls w/ pasture, front porch w/ outdoor seating, garage game room w/ ping pong table brKITCHEN: Cooking basics, Keurig coffee maker, dishwasher, stove/oven, refrigerator, microwave, kettle, toaster, knife block, dishware & flatware brGENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, in-unit washer & dryer, laundry detergent, central heating & air conditioning, iron/board, hair dryer, trash bags & paper towels brFAQ: Optional horse-boarding fee (paid pre-trip), 3 exterior security cameras (facing out) brACCESSIBILITY: Stairs required for access, single-story home brPARKING: Driveway (2 vehicles), horse trailer parking availablebrbr-- THE LOCATION --brbrBEACHES + PARKS: Toms Cove Park (2 miles), Assateague Island National Seashore (3 miles), Chincoteague Beach (3 miles), Chincoteague National Wildlife Refuge (4 miles) brISLAND EXCLUSIVES: Chincoteague Island Farmers and Artisans Market (1 mile), Captain Timothy Hill House (2 miles), Museum of Chincoteague Island (2 miles), Assateague Lighthouse (4 miles), NASA’s Wallops Flight Facility Visitor Center (6 miles)brHIKING + BIKING TRAILS: Island Nature Trail (2 miles), Bivalve Trail (5 miles), Woodland Trailhead (5 miles)brOFFSHORE EXCURSIONS: Captain Dan’s Around the Island Tours (0.8 miles), Daisey’s Island Cruises (0.9 miles), Barnacle Bill’s Wild Pony Boat Tours (3 miles)brFISHING SPOTS + CHARTERS: Downtown Chincoteague Waterfront Park (0.8 miles), Captain Steve’s Bait and Tackle (2 miles), Captain Bob’s Marina (2 miles), Island Queen Inland Charters (3 miles)brAIRPORTS: Salisbury Regional Airport (48 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowed br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Your safety matters. This property features 3 exterior security cameras. The 2 cameras on the outside of the home are not activated and do not record video or audio. There is a camera in the barn facing the horse stalls and pasture for horse safety. This camera actively records video and will be turned on during your stay br- NOTE: This single-story home requires a small set of stairs to access br- NOTE: Optional horse boarding is available for an additional fee paid on-site to the Guest Contact, whose information will be provided after your reservation is complete & paid in full

Bed

Bath

Sleeps

$280.75

/ Nightly

Private Vacation Home

Chincoteague Island Creekside Cottage

Chincoteague, Virginia, United States

Creekside Cottage delivers all the feels...brJuly 2020 USA Today Best Coastal Small Town. Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponies) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124. Make Memories!

3

Bed

2

Bath

8

Sleeps

$538.49

/ Nightly

Private Vacation Home

Coral Cove- Canalfront with Kayaks & Private Dock

Chincoteague, Virginia, United States

Coral Cove- Waterfront Retreat on the Canal in Oyster BaybrWake up to sunrise views & relax on the screened porch at Coral Cove a 3-bedroom, 2-bath waterfront retreat on the canal in Chincoteague's Oyster Bay I community. With bright, open living spaces and a fully equipped kitchen, the home is perfect for family getaways or a peaceful escape. brbrTie up your boat along 100 feet of bulkhead, dock at the 16' fixed pier, or launch kayaks and paddle boards from the private floating dock. Spend the afternoon crabbing in the backyard, grill dinner on propane or charcoal, and dine outdoors on the deck or screened porch. brbrGuests also enjoy access to the community boat ramp, making it easy to explore the waterways of Chincoteague and Assateague. Whether you're hosting a family or simply recharging by the water, Coral Cove is your place to relax and make memories. brbrAmenities ListbrbrBedrooms & Bathroomsbr-3 Bedrooms/Sleeps 9brMain Level: King bedroom with adjacent full bath (tub/shower combination)brUpstairs: Queen bedroombrUpstairs: Bunk room with 2 sets of twin bunks + twin trundle (5 total twins)br2 Full BathroomsbrMain level bathroom (accessible from bedroom & living area)brUpstairs: Jack & Jill Bathroom (tub/shower)brbrLiving & KitchenbrBright & open living & dining spacesbrFully equipped kitchen with modern appliancesbrConvenient laundry room off the kitchenbrCozy indoor sitting area with mini-fridge (ground level)brbrOutdoor Features & BoatingbrWaterfront Retreat on the Canal with sunrise viewsbr100 feet of bulkhead for boat tie-upbrbr16-foot fixed dock (great for small boats & fishingbrFloating dock (ideal for kayaks, paddle boards & canoes)brOversized screened porch overlooking the waterbrSpacious front deck for dining al frescobrCrabbing & fishing right from the backyardbrAccess to community boat ramp (Oyster Bay I)brGuest also have access to 2 small kayaks, crab pots, and some other fun surprises brbrCooking & DiningbrPropane GrillbrCharcoal GrillbrIndoor dining area & outdoor dining spacesbrbrConveniencebrCovered outdoor parkingbrPrivate Outdoor ShowerbrHigh Speed Wi-FibrCentral heating & air conditioning

Bed

Bath

Sleeps

$595.19

/ Nightly

Private Vacation Home

Beautiful Sunsets Over The Chincoteague Bay* Panoramic Water Views* Private Dock

Chincoteague, Virginia, United States

Enjoy Sunday to Sunday weekly summer season rentals in this dynamic 3 level house which boasts panoramic water views from every exquisitely decorated room. Take in stunning sunsets over the Chincoteague Bay from either one of the three large waterfront decks featuring gorgeous brand new outdoor furniture. Fish, crab or boat from the home's private dock or new 64 feet of bayfront boardwalk. Sit on the large screened in porch, which includes a brand new swing, and take in the sunrise over beautiful downtown historic Main Street directly across the Chincoteague Channel. The home features a large open floor plan great for entertaining, sleeps 8 with 3 bedrooms and a brand new queen sleeper sofa in the living room. A futon is also available to accommodate 2 additional guests if needed, as well as a pack and play for little guests. The living room has a large flat screen smart tv with DirectTV for lazy days and there are also tvs in the master and second bedrooms. On the first level there is a half bath and bedroom with 2 twin beds and a private entrance off of the screened porch. On the second level, the master bedroom offers a private bathroom, queen bed and French doors leading to a sunset deck with two rocking chairs. The third bedroom has a double bed and another private bath. There is also a sitting area with lovely bookshelves and stocked with games for your amusement. The third level features a quiet sitting area where you can relax and enjoy a good book or take in the stunning panoramic water views from every window. Bike, walk or kayak to town. Enjoy beautiful Assateague Island National Seashore just a few minutes away. This home promises to make all of your vacation dreams come true.

Bed

Bath

Sleeps

$374.11

/ Nightly

Private Vacation Home

Teague Time by Seaside Vacations & Sales

Chincoteague, Virginia, United States

**Teague Time has a Brand New Fenced Yard for your Furbaby!**brbrThe best things in Life are the people we love, the places we've been, and the Memories we've made along the way. Welcome to Teague Time on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. This beyond-adorable Vacation Cottage is located in popular Piney Island, which happens to be the closest community to Assateague National Seashore. Wild Ponies, Beach Combing, and one of the most gorgeous beaches in our country are just a short stroll or bike ride away! 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.....brbrNo detail has been missed at Teague Time. This delightful Home sleeps 6 very comfortably in 3 lavish Bedrooms. Cute and Cozy, both the Indoor Living and Outdoor Living are just full of surprises. As you enter through the Kitchen, kick off your flip flops and let the fun begin. Relaxing Coastal Colors and fun Nautical Accents instantly let you know that you're on Island Time now. The well-equipped Kitchen has all you need to make mealtime super easy - dine indoors or Al Fresco on the Screened Porch. After dinner, gather around the Fire Pit and share stories of the day's Adventures while listening to the Tree Frogs sing. Can you even remember the last time you were this relaxed brbrAfter a day of exploring Assateague Island and searching for Wild Ponies, relax in the comfy Living Area and enjoy Flat Screen Cable TV and Free WiFi. Or sway in the Porch Swing and listen to the sea breeze rustle the Pines. There are few places as wonderful and serene as Piney Island, that's for sure. This awesome Community even has a natural Kayak Launch, so bring your kayaks along, or let us help you with kayak rental and delivery. There is much to explore in our beautiful waterways!brbrThe Master Bedroom is just off the Living Area and simply stunning. Coastal Style Furnishings and Colors of Sea Glass and Coral will lull you to sleep in the comfy Queen Bed. The Full Size Washer and Dryer are tucked out of sight in the Laundry Closet, conveniently located in the Master. The Master Bath is a work of Art itself with Colors of Sand Dunes, Granite Vanity, and a Custom Walk-in Shower. Bedrooms 2 and 3 are located on the opposite side of Teague Time, giving the Master lots of privacy. Bedroom 2 has 2 Twin Beds, and Bedroom 3 has a Queen Bed - each has its own unique Coastal Flair. They share Sunny Full Bath 2, which has a Tub/Shower Combo and lots of storage. brbrAnd if you're into Outdoor Living, Teague Time is the place for you! The Stone Fire Pit is where every evening will end with memorable stories and lots of giggles. brbrAs you see, Teague Time is not just a place, it's a feeling - a feeling of pure happiness. Traveling with a group Also check out Slack Tide - right next door to Teague Time!brbrWell-behaved dog allowed with $100 Pet Fee. Must be current on all vaccinations and on flea/tick preventative.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.

Bed

Bath

Sleeps

$372.43

/ Nightly

Private Vacation Home

4 bedroom beach house minutes from the beach by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Sand Dollars wash upon the shore like smiles from the Sea…..brbrThe things we treasure most in this life aren’t ‘things’ at all - time with those we love, precious memories made by the seashore - the most valuable treasure to be had. Welcome to Sand Dollar on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. This lovely home is located in popular Piney Island, which happens to be the closest community to Assateague National Seashore. Wild Ponies, Beach Combing, and one of the most gorgeous beaches in our country are just a short stroll or bike ride away! 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.....brbrSand Dollar is a one-of-a-kind Beach Getaway. Perfect for one large family, or for 2 families to share, the layout is just wonderful for spending time together without ever feeling crowded. After a fun-filled day exploring Assateague, you’ll love relaxing in the spacious Living Room with Flat Screen Cable TV, Free WiFi, and plenty of room for all. Soaring ceilings and tons of natural light make it so warm and welcoming.brbrThe Chef in your family will love the spacious Kitchen, well-stocked with all you need. Dine at the huge dining table, or Al Fresco on the Screened Porch while listening to the Tree Frogs sing. Enjoy a glass of wine while the kids chase Lightning Bugs in the backyard. There’s even an Outdoor Shower on the Screened Porch - perfect for rinsing off sandy feet. brbrSand Dollar sleeps 8 more than comfortably. With 2 Bedrooms up, and 2 on the 1st floor, it’s ideal for the way we live today. Bedroom 1 has 2 Twin Beds and is just off the Living Area. Bedroom 2 is just off the Kitchen with a Queen Bed and access to the Laundry Area and Full Bath with Tub/Shower Combo. Wandering upstairs, Bedroom 3 sleeps 4 with 2 Twin Beds and 1 Full Bed. The kids will love this room - lots of space and there’s even a Flat Screen TV. Bedroom 3 has its own Private Bath with Tub/Shower Combo, as does Bedroom 4! Bedroom 4 is super special with a comfy King Bed, another Private Full Bath, and access to a Private Balcony facing the Assateague Channel! Sneak out to stargaze while the rest of the family slumbers, or enjoy your morning coffee while watching Herons and Egrets fish for their morning meal. brbrPiney Island is a beautiful, quiet community - great for long walks, relaxing amongst the shady pines, and there is even a community kayak launch just down the street. Its proximity to the beach and wildlife refuge makes it one of the most desirable locations on our little island. brbrSand Dollar - Today’s precious moments become tomorrow’s precious memories…..brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.

Bed

Bath

Sleeps

$294.55

/ Nightly

Private Vacation Home

Bertie Street Cottage by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Life takes us down many paths, but our favorite ones lead to the Beach. Looking for the perfect Island getaway for your family Welcome to Bertie Street Cottage - adorable and affordable in the heart of the Island. Located in a peaceful, quiet part of our wonderful Island, you'll enjoy the serenity here after a busy day of exploring Assateague Island. Close to everywhere you want to be, with the feeling of being a million miles away.....brbrBertie Street Cottage has had many updates this Fall and has a fresh new look! You'll love relaxing in the cheerful Living Room with hues of Sea Grass Green punctuated with bright pops of reds and blues. Such a great place to gather and share stories of the day's adventures, or perhaps enjoy family movie time on the Flat Screen Streaming Only TV, and of course there's Free WiFi!brbrWe are just in love with the Screened Porch at Bertie Street Cottage - beautifully furnished, you'll feel as if you're on a Tropical Retreat. Dine Al Fresco and listen to the Tree Frogs sing, or indoors in the refreshing AC.brbrThis Cozy Cottage sleeps 5 in 2 Bedrooms. The 1st Floor Master has a comfy Queen, and wandering upstairs you'll find a very cool Loft Bedroom with 3 Twin Beds that just oozes coastal charm. brbrBertie Street Cottage is located off of South Main Street, just a hop, skip, and jump from the beautiful Chincoteague Bay. It's an easy stroll to catch one of our spectacular sunsets - we highly recommend taking in as many of them as possible - truly magical! Give us a call to book your Island Time today!brbrBertie Street Cottage - An exciting New Addition to the Seaside Vacations' Family!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.

Bed

Bath

Sleeps

$247.4

/ Nightly

Private Vacation Home

Blue Skies - SFH - Close to Town - Pet Friendly - Linens and Towels Provided

Chincoteague, Virginia, United States

Amenities: Central A/C, Microwave, 2 TV's with Nextflix (no cable), DVD Player, W/D, Dishwasher, WiFi, Outside Shower, Kayak and Crabbing Supplies. Linens and Towels Provided. brbrEnjoy all that downtown has to offer in this cozy island home within walking distance to shops and restaurants. There is plenty of privacy in this petite home! First floor bedroom features a table and TV, great for hanging out playing games or watching movies while others enjoy the main living space. New Rental with fresh work, paint and new beds. Nice back yard with deck and outside shower. Kayak and Crabbing/Clamming supplies available for guests to enjoy. Allows Pets.. Pet friendly home $75.(per pet) will be added to your reservation. There is a 2 dog limit and 40 lbs or less. This home does provide linens and towels. 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, 3 Twins, 1 DoublebrbrSunday Change Overbrbr2026 Prime Season Rate $ 952 weekly / $ 136 per night with 3 nights minimumbr2026 Off Season Rates $ 826 weekly / $ 118 per night with 3 nights minimumbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

4

Bed

2

Bath

7

Sleeps

$365.33

/ Nightly

Private Vacation Home

The Blue Heron- Close to Beach. Shared Community Water Access.

Chincoteague, Virginia, United States

This spacious home features an open floor plan, ideal for family gatherings and entertaining. Nestled in the woods yet just a short distance from the beach, it offers the perfect blend of privacy and convenience. You’re also close to dining, shopping, bike rentals, and other local attractions.brbrEnjoy the large screened porch, perfect for relaxing or spending time with family. The first floor includes a spacious living room, fully equipped kitchen with dining area, a queen bedroom, a second bedroom with two twins, a full hall bathroom, laundry room, and a half bath.brbrThe second floor offers two additional bedrooms—one with a queen bed and one with two full beds—sharing an adjoining full hallway bath. Guests also have access to the nearby community kayak launch for outdoor adventure.

Bed

Bath

Sleeps

$314.12

/ Nightly

Private Vacation Home

Fiddler on the Creek | Waterfront w/ Lighthouse Views, Kayaks & Dock

Chincoteague, Virginia, United States

Experience the beauty of Chincoteague Island at Fiddler on the Creek, a newly renovated waterfront retreat with stunning views of Assateague Island and the iconic Assateague Lighthouse. This thoughtfully designed coastal getaway combines modern comfort, bright open spaces, and incredible water access for an unforgettable island escape.brbrWake up to spectacular sunrises over the bay, enjoy your morning coffee on the waterfront balcony, and spend your days exploring the waterways, kayaking, or simply relaxing in a serene coastal setting.brbrThe SpacebrbrThe main floor of Fiddler on the Creek is bright and inviting, featuring:brbrOpen-concept living area with comfortable seating and panoramic water viewsbrFully equipped kitchen with brand-new appliances, a breakfast bar, and all the essentials for preparing mealsbrDining room with a large table, perfect for family dinners or game nightsbrBar area with wine fridge, workspace, and convenient half bath for guestsbrbrLarge windows and coastal décor create a light, airy atmosphere that complements the natural beauty outside.brbrBedrooms & BathroomsbrbrUpstairs, the home features two beautifully appointed bedrooms, each with its own private bathroom:brbrWaterfront King Bedroom: Expansive views of Assateague Island, sunrise from the balcony, and luxurious linens providedbrSecond Bedroom: Two queen beds, perfect for family or friends, also with private bathroombrLinen service and towels are provided for up to six guests, ensuring a stress-free staybrbrWaterfront Living & Outdoor ActivitiesbrbrStep outside and enjoy everything the bay has to offer:brbrShared private pier with direct access to the waterbrLaunch kayaks or canoe and explore the scenic waterwaysbrRelax on the spacious waterfront balcony and take in the iconic lighthouse viewsbrPerfect spot for morning coffee, sunset drinks, or watching boats drift bybrbrThis home blends relaxation and adventure, giving you the perfect base to enjoy Chincoteague’s natural beauty.brbrPrime Chincoteague Island LocationbrbrLocated just minutes from restaurants, local shops, bike trails, and the beaches of Assateague Island, Fiddler on the Creek combines quiet, scenic waterfront living with easy access to everything Chincoteague has to offer.brbrWhy Guests Love Fiddler on the CreekbrbrWaterfront location with unobstructed views of Assateague Island and LighthousebrPrivate balcony and shared pier with kayaking and canoeing accessbrNewly renovated, bright, and modern coastal interiorbrPrivate bathrooms in both bedrooms for comfort and conveniencebrIdeal for families or small groups up to 6 guestsbrSpectacular sunrises and serene bayfront ambiancebrbrBook your stay at Fiddler on the Creek and experience the ultimate Chincoteague waterfront getaway—sunrises, sunsets, kayaking, and lighthouse views all included.

Bed

Bath

Sleeps

$242.99

/ Nightly

Private Vacation Home

Whelk-M-Home- Waterfront w/ Shared Deep Water Dock.

Chincoteague, Virginia, United States

Beautifully furnished and offering stunning water views, Whelk-M-Home is an inviting end-unit townhome with access to a shared deep-water dock—perfect for fishing, crabbing, or simply enjoying the sights and sounds of the channel.brbrTake in fabulous sunsets from any of the home’s multiple balconies.brbrThe first level includes a fully equipped kitchen, comfortable dining and living areas, and a convenient half bath.brbrUpstairs, the second-floor queen bedroom features a private waterfront balcony. A full bathroom with a tub/shower combo is accessible from both the bedroom and the hallway.brbrThe spacious third-floor bedroom includes a queen bed, a trundle bed, a cozy coffee bar, and a mini-fridge. A brand-new full bathroom with a shower and bidet adds an extra touch of luxury. Step onto the private balcony for some of the best waterfront views in the home.brbrOn the ground level, the carport offers fantastic outdoor living space with a table, grill, extra fridge, and even a charming fishpond!brbrA wonderful stay awaits at Whelk-M-Home.

Bed

Bath

Sleeps

$381.82

/ Nightly

Private Vacation Home

Fabulous 3 Bedroom House. Peaceful, Relaxing Sunnywood Retreat in Chincoteague.

Chincoteague, Virginia, United States

If rest and relaxation is what you need then Sunnywood Retreat is the place for you! This is a beautiful impeccably maintained house away from the noise and crowds in one of the best neighborhoods on the island but centrally located. When you first arrive you'll notice the stars above and just the sounds of the owls at night. There never was a more peaceful place to get a good nights sleep. This is a neighborhood of old where you don't worry about if your car is locked at night. Of course better safe than sorry. When it comes time for fun everything is a short walk or bike ride away. Beaches, Fishing, Crabbing, Tennis, Main Street Shops, Restaurants, Eco Tours or take in a movie at the historic Island Theater. Something for everyone. brbrThis is a beautiful 3 bedroom home on an acre of property so there is plenty of room to enjoy all the amenities of Sunnywood Retreat. This is a family home we rented to special friends over the years and all enjoyed it immensely. Most booked it year after year. 2025 will be our first year renting on Vrbo and we hope you'll enjoy it too.brbrThe spacebrThe main bedroom has a comfortable queen sized bed with private bath and stall shower. Bedroom 2 has an new queen bed. Bedroom 3 has 1 twin sized bed and one set of bunk beds.brThe Family/TV room has plenty of room to stretch out and relax with a good movie on the 54 inch TV. The large screen porch is an excellent place to see the local deer pass through the yard during breakfast or have dinner in the cool evenings. The formal dinning room has seating for 8. If you have musical skills take a turn at the baby grand piano. There is also a TV in the living room above the gas fireplace.brbrThe kitchen remodeling is being completed by May 1st 2026. Beautiful new floors cabinets and appliances. This remodel included new floors and paint of the Mud room and Family room.brbrOn the large deck is a Private Outdoor Shower, Gas Fire Pit, Patio Furniture w/ Umbrella and Barbecue.brbrThere are several bicycles including one Tandem, Beach Cruisers and Mountain Bike for use while you're on the island. There is also a child's bike cart and Kayak. Please bring your own safety gear. Nothing is out of reach by bike.brbrIn the bike shed you will also find Bocce, Badminton, Crochet, Corn Hole, Horse Shoes, Hammock, 4 Beach Chairs, Crab Net and Crab Trap. brbrThere is a fire pit that you will need to supply your own wood for and follow local fire limitations.brbrThe local park is a short walk or bike ride down the block. While there enjoy the recently renovated Tennis and Basketball courts, Playground, Fishing Pier, Boat Launch or watch the famous Pony Swim. You will love the views of the lighthouse from the fishing pier especially in the evening.

Bed

Bath

Sleeps

$587.78

/ Nightly

Private Vacation Home

Sunset View - 4BR Water Front -Water Access, Gazebo, fire pit LINENS INCLUDED

Chincoteague, Virginia, United States

Amenities: Central A/C, Cable TV, DVD, W/D, Microwave, Dishwasher, WiFi, Porch, Gazebo, Outside Shower, Firepit and Waterview. FLOATING DOCK & PIER.Totally renovated Waterfront Victorian offers classy style with spacious floor plan. Lovely eat in kitchen with dining area overlooking the back gardens and fenced in yard. Big back deck with outside shower. Across the street on the Chincoteague Channel is a lovely gazebo, firepit and sitting chairs. 2 Bikes and 2 Kayaks are available for Guest use. This 4-bedroom home offers Linens and Towels and the best way to enjoy Chincoteague Island. Walking distance to town or carnival grounds. 1st level bedroom and 3 bedrooms on 2nd level. 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). This house is protected by an outside surveillance systembrbr***This property requires BOTH the $1000 Refundable Security Deposit and the $ 70 Non-Refundable Security Protection Plan when renting. ***brbrLINENS AND TOWELS PROVIDEDbrBed Sizes: 3Q,1TbrbrSunday Change Overbrbr2026 Prime Season Rates $ 3451 per week / $ 689 per nightbr2026 Off Season Rates $ 2982 per week / $ 596 per night ( 3 night minimum)brCall Office for last minute availability. brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Bed

Bath

Sleeps

$220.7

/ Nightly

Private Vacation Home

Bays Landing -Dynamic Waterfront Views-Townhouse -LINENS ANDTOWELS PROVIDED

Chincoteague, Virginia, United States

Amenities: Central A/C, Microwave, Dishwasher, W/D, WiFi, Decks LINENS AND TOWELS PROVIDED brbrWaterfront end unit townhouse located on Marsh Island with unobstructive views directly facing the channel.. Dynamic views from every room in this beautiful property. Great views of Chincoteague and the Chincoteague Bay. Enjoy the sunsets from the balconies or kickback and watch a rocket launch without having to go out of the house. You will enjoy every area of this home. Outside decks, fishing table & boat mooring. 2 car garage available for your use, fish table and dock all a step away. Linens and towels are provided. 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: 2 Queen, Full Sleep SofabrbrSaturday Change Overbrbr2026 Prime Season Rate $ 1652 per week ($236 per night) br2026 Off Season Rates $ 1050 per week $ 150 per night 3 night minimum brbrIf you use a credit card there is a 3% Convenience Fee in addition to the charge. ****

Bed

Bath

Sleeps

$199.98

/ Nightly

Private Vacation Home

Turn of the Creek - 2BR home, W/F, Water Access home deck & dock.NO LINENS

Chincoteague, Virginia, United States

Amenities: Central A/C, W/D, Microwave, Dishwasher, Cable, WiFi, Sun Deck, Dock, Gas Fireplace.brbrTurn of the Creek is the perfect spot for those who love to kayak! Beautiful views of Eel Creek and the Marshes that surround it. The property has great outside space from the screen porch, upstairs sun deck to the dock that is perfect for crabbing or just relaxing. br br THIS HOUSE DOSE NOT PROVIDE LINENS AND 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, Bunk with 2 twins, 1 Queen Sleep SofabrbrSunday Change Overbrbr2026 Prime Season Rate $ 1386 per weekbr2026 Off Season Rate $ 952 per week / $ 136 per night with 3 night minimum brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Bed

Bath

Sleeps

$298.73

/ Nightly

Private Vacation Home

Gorgeous duplex with dock by Seaside Vacations & Sales

Chincoteague, Virginia, United States

There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the whole family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague Island to make Memories that you'll treasure forever. And Island Haven is the perfect place to make this happen - the Sun, the Sea, and Views that are simply unforgettable. brbrThis gorgeous Duplex sleeps 8 and is located on desirable Piney Island, the closest community to Assateague National Seashore. Ride your bike to the Beach, Dining, Activities, and more! You'll love returning to this tranquil Waterfront Community lined with whispering Pines, which even has its own Kayak Launch area. Sitting directly on the Assateague Channel, you have incredible Views of both the Channel and Assateague Island right from your two-levels of decking. With its own Private Pier, you'll love fishing and crabbing in your own backyard - or harvest some of our famous Oysters at low tide, only steps from the shoreline. There's also super-easy access to launch your kayak or canoe, and if you're bringing your boat, you can tie it up right at the end of your Deep Water Dock. Island Haven truly has all you need to make your Vacation Dreams come true!brbrAs you pull up to Island Haven, you know you've made the right choice - the Pine Trees swaying and Tree Frogs singing couldn't be more welcoming - and ahhh, that salty, sweet breeze. Climbing the stairs to the 1st Floor, you'll love the Open Living Area with plenty of comfy seating, Flat Screen Streaming TV with Roku, and magnificent Views galore. You'll love beginning and ending every fabulous day on the Screened Porch - and oh, the Sunrises you'll take in here. Island Haven sits high, maximizing every gorgeous glimpse of our beautiful bay and Assateague Island. brbrDown the Hall, there's a huge Dining Area with with a table that seats 8 - a great place to gather and share stories of the day's Adventures. The Chef in your family will love the well-stocked Kitchen will all you need to make mealtime a bay breeze. You can also dine Al Fresco at the Picnic Table while taking in the beauty - what a great place to enjoy some Fresh Local Crabs. And while no one likes doing laundry, you'll appreciate the convenience of the Washer and Dryer on this level, as well. There is also a convenient Half Bath just off the Living Area.brbrWandering upstairs, there are 3 spacious Bedrooms and 2 Full Baths. The Master Bedroom features a comfy Queen Bed, Flat Screen TV with Roku, and access to a Private Waterfront Balcony - slip outside to stargaze while everyone sleeps peacefully, or enjoy morning coffee here with a Sunrise. The Master Bath had a Tub/Shower Combo and lots of storage. Down the Hall, Bedroom 2 has 2 Twin Beds, and Bedroom 3 has a Full Bed. A 2nd Full Bath with a Tub/Shower Combo is located in the Hall. No one will ever feel crowded at Island Haven!brbrWith the Assateague Channel as your backyard, and Assateague National Seashore just a short bike ride away, you really can have it all at Island Haven! Chincoteague and Assateague are a Nature Lover's Dream - perfect for pony-lovers, photographers, and bird-watchers. There's even an Outdoor Shower to rinse off after a day exploring the Beach. You can either bring your own Kayaks, or we're happy to help you arrange for rentals to be delivered! So, what are you waiting for Paradise is calling.....brbrIsland Haven - Relax, Rejuvenate, and Reconnect.......brbrIsland Haven has a Sunday Check-in during the Peak SeasonbrbrNO 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.

Bed

Bath

Sleeps

$250.3

/ Nightly

Private Vacation Home

Pet friendly island home with fenced in yard by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Lily Pad on beautiful Chincoteague Island is the perfect place to make your Vacation Dreams come true. This adorable and affordable Vacation Home is located on the ever-popular East Side, tucked on a quiet street, yet super close to everywhere you long to be. Lily Pad will greet you with an inviting yard and lots of parking for your cars and water toys. brbrThis charming Home sleeps 6 at a very family-friendly price tag. Once you sink into an Adirondack Chair around the Fire Pit and see the breathtaking Views of Assateague Lighthouse, you'll never want to leave! brbrRelax in the Living Area after an adventurous day exploring Assateague National Seashore, and enjoy the comfort of AC, Flat Screen Streaming TV, and Free WiFi. With the quintessential Island Charm you love and the Modern Amenities you need, Lily Pad is sure to please the whole family.brbrFriendly dogs welcome with a $100 Pet Fee each. Max 2 Dogs with Permission. Dogs MUST be current on Flea/Tick Preventative and Immunizations.brbrThe Chef in your family will love the well-stocked Eat-in Kitchen with everything you need to make mealtime a bay breeze. Not one to cook on Vacation Many Dining options are just a short walk or ride away. Or grill the Fresh Catch of the Day while listening to the Tree Frogs sing - the kids will love the huge yard perfect for chasing Lightening Bugs! brbrLily Pad sleeps 6 in 3 comfy Bedrooms. The Master Bedroom has a Queen Bed and Colors of Sea Glass. Down the Hall, Bedroom 2 also has a Queen Bed, and Bedroom 3 has 2 pretty-in-purple Twin Beds. The shared Full Bath is convenient to all Bedrooms and the Living Area, and has a Tub/Shower Combo.brbrAt Lily Pad, the Outdoor Living is just as warm and inviting as the Indoor Living. Just imagine gathering around the Fire Pit, toasting marshmallows, and sharing stories of Chincoteague Island. There's so much to do on our beautiful Island - search for Wild Ponies, simply relax on the Beach, or take a Boat Tour - an awesome way to experience our little slice of Heaven. Whatever your pleasure, Lily Pad is the perfect Home Base!

3

Bed

1

Bath

6

Sleeps

$233.97

/ Nightly

Private Vacation Home

Blue Sky - Pet Friendly- Fenced Yard - No Smoking

Chincoteague, Virginia, United States

2BR/2 B *** ( Bed Sizes) 1 Queen, 2 twin, 2 cots & foam twin size upstairs. Amenities: Amenities: WiFI, Smart TV, Central HVAC, OS Shower, Iron/ Iron Board, Pet Friendly with dog indoor/outdoor kennels, Fenced Yard, Beach Toys, Hair Dryer in each bathroom. Iron board/iron. House will allow 7 occupants but only has 2 bedrooms. br brDescription: Lovely 2BR, 2 Bath home in quiet neighborhood is delightful. Spacious living room, nice fully equipped kitchen, back porch has 2 cots for extra guests. Primary bedroom upstairs has space and bunkie for extra child. Back deck and outside fenced in yard and fireplace. Outside shower, Linens provided. Close to Memorial Park and boat launch area. brbrPlease ask about our cancelation policy. 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).brbrbrBed Sizes: 1Q,2 Twins, Foam bed upstairs under Queen bed is twin size and 2 cots on back porch. brbrChange Over Saturday brbr2026 Prime Season Rate $ 1204 per week / $ 172 per night br2026 Off Season Rate: $1,001 per week / $ 143 per night 3 night minimumbrbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

3

Bed

2

Bath

7

Sleeps

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$250.3

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