Vacation Home Rentals By Owner In Chincoteague, VA

$247.06

Water view • cozy & quiet 2-BR cottage

Chincoteague, Virginia, United States

Recently renovated, located in Chincoteague with bayside water view from your spacious & peaceful covered deck. This is a family oriented fourth generation homestead, nestled in on quiet North Main Street only 6 miles for Assateague Beach, 1.5 miles from down town & only 1 mile from the Island Nature Trail. This charming cottage offers 2 cozy bedrooms - one with a queen bed and the other with 2 twin beds. The bathroom features a refreshing shower and a hair dryer for your convenience. With amenities like heating, WiFi, AC, and an iron, guests can relax and unwind in this gorgeous retreat. Our place is equipped for both long or short stays to make your vacation one to remember.

2

Bed

1

Bath

4

Sleeps

$378.73

/ Nightly

Private Vacation Home

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

$522.89

/ Nightly

Cottage

Pet-friendly creekside cottage w/ backyard

Chincoteague, Virginia, United States

Summary:brbrWelcome to Creekside Retreat - a cozy Chincoteague cottage where quiet mornings, coastal wildlife, and relaxed evenings come together for an easy island escape.brbrbrbr- Sleeps 6 | 3 bedrooms | 4 beds | 2 bathsbrbr- Private creekside backyard w/ patio & grillbrbr- Sunroom + screened-in porch for year-round relaxingbrbr- Fast WiFi & dedicated workspace for remote workbrbr- Fully equipped kitchen & bathroom essentialsbrbr- Pet-friendly & close to Assateague Island beachesbrbrbrbrThe Space:brbrMorning light filters through the sunroom as birds gather along the quiet creek behind the house, and the island feels unhurried even in the cooler months. Crisp coastal air, rustling reeds, and the gentle movement of water create an easy rhythm for slow mornings and relaxed evenings.brbrbrbrThe cottage at a glancebrbrThis entire cottage in Chincoteague offers a comfortable, grounded retreat for couples, families, or small groups of friends. The home accommodates up to six guests with three bedrooms and four beds, along with two full bathrooms. Single-level living means no interior stairs, making it easy to settle in and feel at home from the moment you arrive.brbrbrbrIndoor spaces to unwindbrbrIndoor spaces are designed for lingering. The front sunroom and the screened-in porch provide two distinct places to unwind - whether you’re reading with a warm drink, watching the creek, or simply enjoying the quiet. Central heating keeps the home comfortable, and WiFi supports streaming, remote work, or video calls. A dedicated workspace in a room with a door makes it easy to balance downtime and productivity.brbrbrbrKitchen, dining, and essentialsbrbrThe kitchen is fully equipped for preparing meals at home, and the dining areas invite long, shared dinners after a day exploring the island. Bedroom and bathroom essentials are provided, including linens and towels, so you can pack light and settle in quickly. Laundry is available in the building for added convenience, especially for longer stays.brbrbrbrOutdoor living by the creekbrbrOutdoor living remains a highlight year-round. The private, fully fenced backyard opens to the creek, where herons, egrets, and other coastal wildlife are frequent visitors. After rain, the yard may be wet, and being close to the water means bug repellent can be helpful at times. The patio, & grill offer a simple way to enjoy the outdoors even in cooler weather. Free on-site and off-site parking is available. brbrbrbrPet-friendly conveniencebrbrThe cottage is pet-friendly, and dogs are welcome. Cats are not allowed. Self check-in with a smart lock and free parking on the premises make arrival and departure easy.brbrbrbrExploring ChincoteaguebrbrLocation is a major part of the experience. Assateague Island and the National Seashore are less than a 15-minute drive away, offering access to beaches, trails, and the famous wild ponies. On the way, you’ll pass through downtown Chincoteague with its local shops, cafes, and restaurants - close enough for convenience, yet far enough to return each evening to a quieter lane by the creek.brbrbrbrWho this space is forbrbrThis space suits travelers who appreciate nature, a relaxed atmosphere, and the simple comforts of a well-equipped coastal cottage.brbrbrbrNotebrbrThe backyard and creek are great for spending time outside. Please do know that after rains, the yard may be wet. Also, if you'll be spending time at the creek, many of our guests find bug-repellent helpful. This comes with the territory of being coastal and having a creek, of course!brbrbrbrWe often take our three little kids and dog to the cabin with us, so we're very family- and dog-friendly. Unfortunately we don't allow cats (we're allergic).

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

$245.95

/ Nightly

Condo

Gorgeous waterfront condo with stunning sunset views by Seaside Vacations

Chincoteague, Virginia, United States

Sunset Bay 307 - Sometimes you just have to go with the Waves…..brbrWelcome to Sunset Bay 307 - Picasso - at fabulous Sunset Bay Villas on the Chincoteague Bay - truly a work of Art! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop and dine in the Historic District. Picasso offers the Luxury you want, the Amenities you need, and even a Pool, all at a family-friendly price! There's even a Private Boat Slip - Boats must be 20 ft. or less. brbrAs you enter this lovely Condo, you’ll be greeted by warm Colors of Sand with fun pops of Nautical Reds throughout .This lovely 3 Bedroom Waterfront Condo sleeps 6 in 3 Bedrooms, in both comfort and style. The open layout is perfect for spending time with those who matter most without ever feeling crowded.brbrYou’ll love relaxing in the spacious Living Area and taking in fabulous Views of the Marina and Chincoteague Bay, right from the comfy Leather Furnishings! Enjoy Flat Screen TV with HBO, Showtime, Cinemax, NFL network with NFL RedZone and Free WiFi as you sink into the comfy furnishings after a fun-filled day searching for ponies, or playing on the Beach at Assateague National Seashore, only minutes away. Or, relax on the Waterfront Balcony and watch Herons, Eagles, and Egrets fish for their morning meal. Picasso is located on the 3rd Floor, maximizing brilliant Views of the Chincoteague Bay. Sunset Bay offers water access just steps away - try your hand at fishing or crabbing on the Community Pier (gear not provided). And, don’t forget about the Bayfront Pool - you will love taking in that salty, sweet sea breeze and a refreshing dip on a hot Summer day!brbrThe Chef in your family will adore the Well-Stocked Kitchen with all you need to make mealtime super easy. Not one to cook on vacation We’ve got you covered - many awesome dining options are just a short stroll down the street in the Historic Main Street District, or a short car ride away. And if you’re worried about those extra Vacation calories, you can burn a few off in Sunset Bay’s Fitness Center.brbrSunset Bay 307 - Picasso - has 3 spacious Bedrooms and 2 Full Baths. Bedrooms 1 and 2 both have comfy Queen Beds and are decorated with a Coastal Flair. Down the Hall, the Master Bedroom features a King Bed and breathtaking Water Views, and is adorned with sophisticated Ivory and Black. With Private Access to the Waterfront Balcony, you can slip out to stargaze while everyone else slumbers. The Spa-like Master Bath has a Walk-in Shower, Soaking Tub, and Double Vanity. A 2nd Full Bath with Tub/Shower Combo is convenient to Living Area and Bedrooms 1 and 2.brbrAs you can see, Life at Sunset Bay Villas is not about having a place to simply lay your head at night, it's a Vacation Experience. From sharing stories of the day's Adventures by the water's edge, to frolicking by the Pool and on the Beach, your time here is about reconnecting with those who matter most and leaving with unforgettable Family Memories.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.

4

Bed

3

Bath

8

Sleeps

$148.35

/ Nightly

Condo

Assateague Inn 206 by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible. brbrOur Studio Suites have a Private Bedroom with queen size bed, and a separate living room with queen sleeper sofa. There is also a spacious Full Bath, and a Kitchenette fully equipped with cookware and dishes, 2 burner stove top, mini refrigerator, coffee maker, toaster and eating area. Our Studio Suites accommodate up to five guests. Relax in the AC and enjoy Flat Screen Cable TV and Free WiFi after a fun-filled day on the Beach, or slip out to the refreshing Pool to cool off. brbrThe Inn is located directly on the Creek, and is a great spot for Crabbing, or simply taking in the Herons and Egrets fishing for their morning meals. Located just off of Maddox Boulevard, you're only a short bike or car ride from Mini Golf, Dining, and of course, Assateague National Seashore! When you're not enjoying playing on the waterfront, relax on the huge landscaped greens with plenty of Picnic Tables and Barbecue Stations to cook up the Fresh Catch of the Day. brbrWhatever your pleasure on beautiful Chincoteague Island, the Assateague Inn is the perfect home base. Give us a call and let us help you plan your Adventure today!brbrbrThe use of amenities- pool and pier-not guaranteed and refunds will not be given due to closure. Please check with us for current status.brbrbrAssateague Inn 206 - Your Retreat on the Creek.....

Bed

Bath

Sleeps

$219.86

/ Nightly

Condo

Assateague Inn 102 by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Assateague Inn 102 had a facelift for 2025, and is beachy and beautiful - check it out!brbrAhhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it Or maybe you're one who prefers to take many shorter trips over the course of the year - a Weekend Warrior, if you will If so, the Assateague Inn was made for you. Whether you'd like to visit for 3 nights or 11, we're here to make your time in Paradise as memorable as possible. brbrOur Studio Suites have a Private Bedroom with queen size bed, and a separate living room with queen sleeper sofa. There is also a spacious Full Bath, and a Kitchenette fully equipped with cookware and dishes, 2 burner stove top, mini refrigerator, coffee maker, toaster and eating area! Our Studio Suites accommodate up to five guests. Relax in the AC and enjoy Flat Screen Cable TV and Free WiFi after a fun-filled day on the Beach, or slip out to the refreshing Pool to cool off. brbrSuite 102 has been beautifully updated with lovely laminate flooring, fresh paint, new bedding, and more. brbrThe Inn is located directly on the Creek, and is a great spot for Crabbing, or simply taking in the Herons and Egrets fishing for their morning meals. Located just off of Maddox Boulevard, you're only a short bike or car ride from Mini Golf, Dining, and of course, Assateague National Seashore! When you're not enjoying playing on the waterfront, relax on the huge landscaped greens with plenty of Picnic Tables and Barbecue Stations to cook up the Fresh Catch of the Day. brbrWhatever your pleasure on beautiful Chincoteague Island, the Assateague Inn is the perfect home base. Give us a call and let us help you plan your Adventure today!brbrThe use of amenities- pool and pier-not guaranteed and refunds will not be given due to closure. Please check with us for current status.brbrAssateague Inn 102-S - Your Retreat on the Creek.....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

$147.44

/ Nightly

Condo

Assateague Inn 100 by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Welcome to The Assateague Inn in the heart of Chincoteague! The Assateague Inn has been a fan-favorite for Chincoteague Lovers for years. Located less than 5 minutes from Assateague National Seashore, and allowing short stays all year long, it’s the perfect Vacation getaway for singles, couples, or small families. brbrAssateague Inn 100-2R is actually 2 awesome Assateague Inn Rooms with an adjoining door for privacy! Just perfect for a small family, 2 couples, or 2 singles traveling together, yet wanting their own space and privacy. Newly Renovated in 2023, it’s absolutely beautiful, has so many updates. brbrAs you enter, you'll instantly feel in “vacation mode” - Crisp Whites and Nautical Blues are welcoming, and you’ll love the tasteful Nautical Decor throughout. Each Room is beautifully furnished and appointed, and each has its own Kitchenette equipped with all you need to make mealtime a bay breeze! It is also one of the few here at the Inn that actually has an Oven - and Assateague Inn 100-2R has TWO!brbrEach Room is also equipped with a comfy Queen Bed, Flat Screen Cable TV, its own Private Full Bath, and even a Vanity. Relax in the AC and enjoy Flat Screen Cable TV and Free WiFi after a fun-filled day on the Beach, or slip out to the refreshing Pool to cool off. Or slip out to catch some Crabs on the Dock!brbrThe Inn is located directly on the Creek, and is a great spot for Crabbing, or simply taking in the Herons and Egrets fishing for their morning meals. Located just off of Maddox Boulevard, you're only a short bike or car ride from Mini Golf, Dining, and of course, Assateague National Seashore! When you're not enjoying playing on the waterfront, relax on the huge landscaped greens with plenty of Picnic Tables and Barbecue Stations to cook up the Fresh Catch of the Day. brbrWhatever your pleasure on beautiful Chincoteague Island, the Assateague Inn is the perfect beach break without breaking the bank. Give us a call and let us help you plan your Adventure today! brbrAssateague Inn 100-2R - Your Retreat on the Creek.....brbr*Seasonal Outdoor Pool - dates subject to change*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

$295.73

/ Nightly

Condo

Escape to Chincoteague, just 7 mins from wildlife refuge With a boat slip.

Chincoteague, Virginia, United States

Charming towns like Chincoteage offer you the chance to enjoy the stunning views of this two-bedroom apartment. Located just a 7-minute drive from the Chincoteague National Wildlife Refuge and a 10-minute drive from the Assateague Lighthouse, this property offers the perfect home base for your seaside adventures. brbrAs a traveler, you'll delight in the free WiFi and smart TV, allowing you to stay connected and entertained during your stay. The fully stocked kitchen, complete with a stove, oven, refrigerator, dishwasher, and more, invites you to prepare delicious meals, including fresh seafood from the local markets. Unwind in the cozy living room or step outside to the porch and enjoy the salty sea breeze. For the little ones, the property offers an outdoor play area and games to keep them entertained. Board your boat, kayak or other watercraft right outside your back door with dedicated dock space.brbrWhether you're seeking a relaxing beach getaway or an adventure-filled vacation, this Chincoteague condo has everything you need to make the most of your time on the Eastern Shore.brbrSome renters have missed the amenities we offer. We do not supply any linens ( sheets,towels, wash clothes, dish wash rags or any toiletries ). Sorry for any misunderstanding but we try to supply the cleanest unit available. We don't supply items that can be easily stained and appear soiled even though they have been washed.

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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.

4

Bed

1

Bath

8

Sleeps

$442.86

/ Nightly

Condo

Sunset Bay Villa #202- Waterfront, In Town, Pool & Gym

Chincoteague, Virginia, United States

This gorgeous, fully updated condo is located directly on the bay, offering stunning waterfront views and a front-row seat to wildlife, passing boats, and breathtaking sunsets from your private bayfront balcony. Guests can also enjoy the seasonal bayfront pool and an on-site fitness room for added convenience and relaxation.brbrSituated on the second floor with elevator access, the condo features a stylish, open, and light-filled floor plan that maximizes the spectacular views. The king suite offers waterfront vistas and shares deck access with the living room. Its en-suite bathroom includes a jetted tub, separate shower stall, and double sinks for a touch of luxury.brbrThe second bedroom has a queen bed and an adjacent hallway bath, while the third bedroom features a full bed and a trundle, making the condo ideal for families or groups. Guests can also crab or fish from the private community dock area, combining comfort and coastal living in one exceptional property.

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Bath

Sleeps

$158.51

/ Nightly

Cottage

Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

Chincoteague, Virginia, United States

New Rental ! More Photos and information coming soon. Cozy pet friendly cottage, with 2 bedroom and 1 bath. Each bedroom has a queen size bed and queen sleeper sofa in living room. Within walking distance to Memorial Park and boat launch.brbr Pet friendly home. $75. (Per pet) will be added to your reservation. LINENS AND TOWELS PROVIDEDbrbr***This Property accepts Small and Medium Dogs Only***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, QSSbrbrSaturday Change Overbr br2026 Rate Prime Season: $ 777 per week / $ 111 per night with 3 night minimum br2026 Rate Off Season: $ 679 per week / $ 97 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. ****

2

Bed

1

Bath

6

Sleeps

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