Vacation Home Rentals By Owner In Chincoteague, VA

It is a unique and cozy waterfront cottage with the most amazing view of the National Park, the wildlife Refuge, the lighthouse and the spot where the wild Chincoteague ponies hang out! This cottage is a part of 10 cottages complex. It is a quiet, relaxing location and only 5-10 minutes drive to the town or the beach.

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

Chincoteague, Virginia, United States

2

Bed

1

Bath

4

Sleeps

$254.12

Looking to get off the beaten path Want to truly unwind on beautiful Chincoteague Island This quaint coastal cottage sits just off East Side Road, tucked down a private drive on Tarr Lane. Here, you’ll find the peace and solitude you’ve been searching for.brbrTwinkle Twinkle Little Tarr has been lovingly renovated with your comfort in mind. Vaulted ceilings, an airy open layout, and luxurious finishes will have you wishing for a few extra days. The interior features coastal board-and-batten accents, upgraded appliances, quartz countertops, a farmhouse sink, and a well-equipped kitchen.brbrThe queen bedroom offers direct access to the screened porch—a perfect place for morning coffee or evening relaxation. A beautifully updated full bathroom is conveniently located off the hall. Linen service is included for all beds, plus towels for four guests.brbrStep outside and enjoy the charming outdoor dining area with a gas grill. As night falls, the entire property glows under string lights, creating a cozy, magical atmosphere beneath the mature trees.brbrA serene retreat—ideal for those who want to slow down, breathe deep, and savor Chincoteague.

Twinkle Twinkle Little Tarr- Secluded Coastal Retreat Near East Side

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$314.12

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.

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$242.99

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.

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$204.02

(New Housekeeping Service 2025)br3 bedroom, 2 newly remodeled full bathroom mobile with our large screened in porch with Roll down Sun Shades for when you want to block direct sunlight and for added privacy. We have very nice Multi Setting's Lighting nicely hung in and around entire area of the porch for relaxing, subtle moments or just hanging out having fun. A large multi speed ceiling fan. On this porch is where you get the best view of every island Sunset and an open air sun deck for entertaining or just relaxing. A fire pit for good times around the fire, roasting marshmallows, smores or just getting lost by staring into the fire . A brand new(2022) large propane grill with picnic table and area for outdoor dining. Full eat in kitchen, living room with flat screen tv, DVD player etc. and only 2 blocks from bay/marina where you can drop in your kayaks, about 2-3 miles from refuge and ocean. New central air unit, comfy new beds, large yard, 3 car driveway, private property, etc. This is an ideal area for all that the island has to offer. Just far enough away for peace and quite but, close enough to all the family excitement the island has in abundance. Also, this location is far enough away from island lights in town that gazing into the night skies becomes an amazing experience with thousands of stars beyond anything you've ever seen. Stay once, you'll want to return! ** Attention:** July is the busiest month on the entire island due to our Month Long Carnival and our World Famous, Chincoteague Pony Swim. People come from all around the world to experience the pony swim! It's truly a magical time for all adults and especially the children to witness.brbrbr *** (Attention:)*** Rates during Pony Swim Week Tues. July 26 thru Aug.1 2023br(*** Our Property Included***) Rooms/Hotels etc. are much higher that week due to overwhelming demand for vacancy's throughout the entire island! Most places are Sold-Out month's in advance for July so, Bookings Are Very Limited everywhere on the island. Don't wait to book your time or you may miss out. We work hard at making your stay easy and relaxing. We've begun booking a few dates for the upcoming Spring/Summer of the 2023 season as of this day of February 23, 2022. We look forward to booking our cozy island home with your family. brbrFeel free to contact us about questions etc. We are easy going and available to help answer your questions. Tim & Julie (443) 977-5669brbrThank You.brbrbrbrbrbr

Mobile Home

A Gem By The Sea for your family. (New Housekeeping Service)

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$381.82

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.

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$587.78

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. ****

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$220.7

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. ****

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$241.64

Note; This is a 7 night rental Saturday to Saturday. Charming waterman’s cottage with limited water-views. Walking distance to deli. Close to boat tours. Walk or bike into downtown shopping. Watch the sun set from the screened in porch and new balcony! Star gazing. Pub style outside table and chairs for your own private toast for two! Come for the rocket launches! Ponies walk past the home during Pony Penning!

Oysterhaven Cottage with partial Water views! New balcony! Close to Fairgrounds!

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$199.98

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. ****

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$298.73

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.

Gorgeous duplex with dock by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$250.3

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!

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

Chincoteague, Virginia, United States

Bed

1

Bath

6

Sleeps

$233.97

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. ****

Blue Sky - Pet Friendly- Fenced Yard - No Smoking

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$494.12

Our Chincoteague cottage, is perfect for a relaxing beach vacation or an off-season getaway from life's hustle and bustle. Comfortably spacious for up to 4 guests. We do not allow pets. brbrThis recently renovated cottage features 2 bedrooms, both with king beds. The primary suite has an ensuite bath. There is a spacious kitchen with breakfast bar, dining table, and internet for streaming. Enjoy the provided board games, cards or jigsaw puzzles.brbrOur 3-season back porch and outside patio are perfect for lounging after a day at the beach. Behind the house has been home for an aerie of Bald Eagles. So far we have counted 6 different members. Let us know if you count more!! The patio is equipped with a firepit, propane grill, and ample seating.br brThe cottage is centrally located on the island and is close to restaurants, natural trail, tennis courts, boat ramps, mini-golf, and most importantly the Assateague Seashore refuge, home of the Chincoteague Wild ponies and in our opinion, the best beach in Virginia!. Ocean City Maryland is only about an hour away for boardwalk fun!brbrDiscover the beauty of Chincoteague from this adorable property. Designed to create a comfortable atmosphere where you can relax and unwind after a day of exploring, playing on the beach, enjoying water activities or just lounging. We hope you enjoy our family place as much as we have over the years.

A charming recently renovated 2BR, 2BA home! Pony Penning Week Available

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$312.84

Amenities: New Pet Friendly Rental for 2025 Season. DOGS ONLY, Central HVAC, Internet, Linens and Towels Provided. brbr4 BR Pet friendly home, close to town and short drive to the beach. Fenced in back yard and sleeps 8-10. 3 bedrooms downstairs and 4th bedroom upstairs with sitting area, perfect for kids. brbrPet friendly - Dogs Only. NO SMOKING OR VAPING . Linens and Towels are provided with this property.brbrPet friendly home $75. (per pet) will be added to your reservation. Dog Only. Three night minimum all year round. 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: brbrSaturday Change Overbrbr2026 Prime Season $ 229 per night / $ 1603 for week ( 3 night minium)br2026 $ 1806 for week with 7 night minimumbrbrbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ***br***Month to Month availability***

Jester House - 4BR, fenced yard- Pet Friendly- Linens and Towels Provided

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$444.52

Relax and unwind at one of the most beautiful waterfront townhomes overlooking the Chincoteague Channel. With the living room and master bedroom balconies overlooking the Chincoteague Channel, you will take in some of the most peaceful sights Chincoteague has to offer. Every room boast a relaxing water view, with the ability to view both the sunrise and sunset. When you stay here you will really say life is better on the water.brPlease let us know if you would like to rent the boat slip when making the reservation this will be $100 added to the reservation.br*BREAKING NEWS* SEA GATE ANNOUNCES WITH SPRING IN FULL BLUSH AND SUMMER JUST AROUND THE CORNER WE ARE EXCITED TO OFFER THE AVAILABLITY OF LEVEL 2 ELECTRIC CHARGING FOR ANY OF OUR GUESTS WISHING TO VISIT CHINCOTEAGUE BUT CONCERNED ABOUT WHERE THEY CAN CONVENIENTLY REGHARGE THEIR EV’S WHILE ON THE ISLAND AND IN PREPARATION OF RETURNING HOME. OUR CHARGE IS PRIVATELY LOCATED IN OUR 2 CAR GARAGE. THERE IS A $64 SUR-CHARGE PER CAR.

STUNNING WATERFRONT VIEWS!

Chincoteague, Virginia, United States

Bed

Bath

6

Sleeps

$430.15

Nestled in the shade of tall pine trees in the private community of Oyster Bay, Pearl in the Pines is a charming coastal retreat equipped to meet any need. This bright and beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly, making it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood.brbrYou're on island time at “Pearl in the Pines”. This delightful beach house has an open-concept living area, comfortable furnishings, a spacious screened porch, an outdoor fire pit, and beach-inspired decor that echoes the island's laid-back vibe. brbrWhether you choose to spend your days lounging on the beach at the Assateague Island National Seashore, exploring Chincoteague National Wildlife Refuge (home to the famous Chincoteague ponies), enjoying the island’s eclectic shops and unique restaurants, hiking, bicycling, kayaking, crabbing, or fishing; this is the ideal home base for your island adventures.brbrBedroom 1 includes a full-size bed and a small bathroom with a shower. Bedroom 2 includes a queen-size bed, large closet and a TV. Bedroom 3 includes 2 twin-size beds and a TV. A full bathroom sits across the hall from Bedroom 3. Bed linens and bath towels are included with your stay.brbrAlso included with your stay are 4 adult-size bicycles, 2 kayaks with carts, life jackets, walkable access to the nearby Community Boat Launch, and free EV charging.brbrPearl in the Pines is located approximately 2.0 miles/5 minutes from the center of downtown Chincoteague and 5.0 miles/15 minutes from the Chincoteague National Wildlife Refuge and the Assateague National Seashore (beach).brbrPet fee: $15/nightbrbrCheck-in is at 4:00 p.m. on the day the booking begins.brCheck-out is at 10:00 a.m. on the day the booking ends.

Pearl in the Pines – Bikes, Kayaks, EV Charger, Screened Porch, Fire Pit, Pets

Chincoteague, Virginia, United States

Bed

2

Bath

6

Sleeps

$155.35

This cozy, freshly renovated cottage is perfect for families and friends to have an island getaway. Less than 2 miles away from Chincoteague's main attractions, and only a few minutes drive to the beach, this is the perfect vacation spot. brThis spacious 450 sq. ft cottage features an open concept floor plan, with one bed room and bathroom. A queen bed in the main living area, and a bunk bed with a full and single bed in the bedroom.The outside offers a screened in porch, outdoor charcoal grill, outdoor shower.brbrbrLinens for bed and bath will NOT be provided. brThere will be a 100.00 per night extra charge for any emotional support animals.brYou will be sent check in information a few days before your staybrbrPlease try to leave cottage as clean as you would expect it for your stay, the next guest and the owner will greatly appreciate your cooperation.brbrHere is a link to my other propertiesbr1999395br4980766

Island Time Cottage

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$270.27

Amenities: 3BR/2B*** {1Q, 1D, 2T, QSS } Amenities: WiFi, Roku TV, Microwave, Dishwasher, Central HVAC,W/D, TV, Deck, Grill, Pet Friendly brbrVacations are about making memories; this home has lots of memories come add a few of your home. This wonderful floor rancher is handicap accessible by ramp. Store your beach gear or bikes in the garage. Three bedrooms and 2 bathrooms with a nice living area, dining area and kitchen. New dishwasher for added convenience while on vacation. This charming home is located just a short distance from Memorial Park where you can walk, ride a bike, fish or crab from the community pier. Launch a boat or just enjoy the breeze. Relax and enjoy your vacation making memories that will last for years to come. Pet Friendly Home, 2 dog maximum mid-size dog or 1 cat. $ 75 Pet Fee Per Pet. brbrThis house is protected by an outside surveillance system. Window AC's in all the bedrooms. 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: 1Q, 1D, 2T, QSSbrbrSunday Change Overbrbr2026 Rates $ 1400 per week / $ 200 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. ***

Mom and Dad's Sweet Memories - Single home - Pet Friendly, NO LINENS PROVIDED

Chincoteague, Virginia, United States