Vacation Rentals By Owner In Chincoteague, VA

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

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

Chincoteague, Virginia, United States

Bed

Bath

8

Sleeps

$492.25

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

Stately Home on Chincoteague Island - Professionally Sanitized

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$201.11

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

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$280.59

3BR/2B***(Single Level Home) {2Q, 1Bunk w/2T} Amenities: Central A/C, Microwave, Cable, WiFi, W/D, Screen Porch, Deck, Barbeque Grill, Outside Shower, Handicap Accessible with a ramp and handicap shower. A $75.00 pet fee per dog will be added. brbrAmenities: Central A/C, Microwave, Cable, WiFi, W/D, Screen Porch, Deck, Gas Grill, Outside Shower, Handicap Accessible with a ramp and handicap shower.brbrShuckers Tump is a pet friendly home, located in town within walking distance to shops and restaurants. Handicap Accessible with a ramp and handicap shower. Formerly known as Cowboy Cottage. This home is open and bright with easy access to all island attractions. brbrThis Property accepts Dogs Only (limit 2)brLINENS AND TOWELS PROVIDEDbrbrCancellations made 30 days prior to arrival will receive 100% of refund of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid. If less then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brBed Sizes: 2 Queens, 1 Bunk Bed w/2 TwinsbrbrSunday Change Overbrbr2026 Prime Season Rate $ 1505 per week / $ 215 per night ( 3 night minimum)br2026 Off Season Rate $ 903 per week / $ 129 per night (3 nights minimum) brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

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

Chincoteague, Virginia, United States

3

Bed

Bath

Sleeps

$281.64

Stunning Cape-style home with sweeping views of the marshes and the Assateague Channel. It’s just a short stroll to waterfront Memorial Park, yet tucked away in a peaceful, secluded setting. Memorial Park offers a fishing pier, playgrounds, basketball and tennis courts, a kayak launch, and more—everything you need for fun-filled days by the water.brbrThe large fenced-in side lot is perfect for outdoor activities. Inside, the open-concept layout is beautifully furnished and thoughtfully equipped. The main-level living room opens onto a spacious screened porch overlooking the wetlands, creating a serene backdrop for relaxing or dining outdoors. The kitchen, dining area, and a full bathroom with a shower stall are also conveniently located on the main level.brbrUpstairs, the king bedroom and a second bedroom with a pyramid bunk (twin over full) plus an additional twin each have access to an open sundeck with fantastic views. A handy second-level coffee bar makes mornings extra enjoyable. A full bathroom with a tub/shower combo is located off the hallway.brbrA peaceful retreat with fabulous views and a prime location—perfect for your Chincoteague getaway.

Cottage

Seadar- Secluded Cottage w/ Beautiful Views

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$205.05

Calling all beachgoers for Chincoteague Island fun! This cozy beach cottage is the ideal abode for your next East Coast adventure. Enjoy days with your toes in the sand and a cold beverage in hand on Chincoteague Beach. Charter a fishing boat and cast a line for the catch of the day or take in the sights of the island from one of the local tours. You also won't want to miss the fresh seafood at the local eateries, just a hop, skip, and a jump from your front door. Chincoteague adventures await!brbr-- THE PROPERTY --brbrFree WiFi | Proximity to Beach | In-Unit LaundrybrbrThis cozy beach cottage is ready to welcome small families or groups for adventures on Chincoteague Island.brbrBedroom 1: King Bed | Bedroom 2: Queen Bed, Twin DaybedbrbrKITCHEN: Fully equipped, Keurig coffee maker, dishware & flatware, spices, under-counter fridge, gas rangebrOUTDOOR LIVING: Front porch, lounge seating, yard space brINDOOR LIVING: Smart TV, dining table, hardwood flooring, beach decorbrGENERAL: Towels, linens, complimentary toiletries, central air conditioning/heatbrFAQ: Access only by stairsbrPARKING: Driveway (2 vehicles)brbr-- THE LOCATION --brbrBEACHES + PARKS: Chincoteague National Wildlife Refuge (1.7 miles), Assateague Island National Seashore (1.7 miles), Chincoteague Island Public Beach (2.0 miles), Toms Cove Park (2.8 miles)brISLAND EXCLUSIVES: Chincoteague Island Farmers and Artisans Market (0.3 miles), Captain Timothy Hill House (1.2 miles), Museum of Chincoteague Island (1.3 miles), Assateague Lighthouse (2.6 miles), NASA Wallops Flight Facility Visitor Center (5.3 miles)brHIKING + BIKING TRAILS: Island Nature Trail (1.1 miles), Bivalve Trail (3.7 miles), Woodland Trailhead (3.7 miles)brOFFSHORE EXCURSIONS: Captain Dan’s Around the Island Tours (0.4 miles), Daisey’s Island Cruises (0.5 miles), Barnacle Bill’s Wild Pony Boat Tours (3.3 miles)brFISHING SPOTS + CHARTERS: Downtown Chincoteague Waterfront Park (0.5 miles), Captain Steve’s Bait and Tackle (0.6 miles), Capt. Bob’s Marina (2.8 miles), Island Queen Inland Charters (3.4 miles)brAIRPORTS: Salisbury Regional Airport (47.2 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 allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs for entry and to access some sleeping arrangements and may be difficult for guests with limited mobility

Cottage

Chincoteague Island Cottage ~ 2 Mi to Beaches

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$168.44

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

3 bedroom home near Maddox Blvd by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$182.46

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

Budget friendly Chincoteague townhome by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$506.24

Beautiful bayfront home located in the quiet community of Richardson's Landing. Enjoy stunning expansive views from every level and unforgettable sunrise panoramas over the water.brbrThe private dock sits directly on the bay and includes a lower stationary platform ideal for launching kayaks. Wooden steps along the side bulkhead offer easy access into the shallow waters. After a day on the bay, relax and unwind around the waterside firepit.brbrThe main level features a fully equipped kitchen, a large dining area, and a comfortable living room. A private den with a sofa, TV, and deck access offers an additional space to relax. Both the first- and second-story decks span the entire length of the house, providing amazing waterfront views.brbrThe first floor includes one bedroom with two twin beds and a shared full bath in the hallway.brbrOn the second floor, the king bedroom features a private full bath and access to the waterfront deck. The queen bedroom also opens to the waterfront deck. A fourth bedroom offers two twin beds, and a shared full bath is located in the hallway.brbrYou’re sure to fall in love with this peaceful, quiet, kayakers’ paradise—yet you’re still just a short drive from downtown Chincoteague, restaurants, the movie theater, the waterfront park, and more.

Moondance- 4BR Waterfront | Private Dock | Screened Porch

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$311.91

Sunset Bay Villa 209...brbrTravel is the only thing you buy, that makes you richer.....br br SUNDAY CHECK-IN DURING PEAK SEASONbr br Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, & the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons & Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop & dine in the Historic District. Sunset Bay Villa 209 offers the Luxury you want, the Amenities you need, all at a family-friendly price - and life is always a little happier when the family dog can come along!br br Sunset Bay Villa 209 just screams 'Luxury Vacation' - upon entering, you'll fall in love with the Serene Colors of Sand & Sky. Both refreshing and relaxing, you'll know what a special place this is - a Tropical Oasis on Chincoteague Island. Kick off your Flip Flops in the spacious Foyer with Custom Tile, and let the adventure begin!br br This gorgeous Watefront Home sleeps 6 Adults and 2 Children in pure comfort and style. The Open Concept Living Area is light & bright, with plenty of room for everyone - spend time together without ever feeling crowded. The thoughtful Owners have truly provided everything to make your Vacation picture-perfect. From high-end furnishings to the most well-stocked Kitchen we've seen, Sunset Bay 209 truly has it ALL. Relax after a fun-filled day at the Beach and enjoy the 65 inch Flat Screen Cable TV/DVD with Google Chromecast - and you'll take in truly amazing Views right from the sofa! Need to do a little work while you're here No problem - Sunset Bay 209 offers Free WiFi with 2 Access Points. There is even a Bose Internet Connected Speaker so you can listen to some Jimmy Buffet by the Bay.....br br Just off the Living Area, step onto the beautifully furnished Balcony and gaze at the Chincoteague Bay. Whether dining or simply relaxing, you won't want to leave this amazing Outdoor Living Area. There is comfy furniture to curl up with a good book, and a Dining Set if you prefer to dine Al Fresco. Speaking of dining, the Chef in your Family will adore the well-equipped Kitchen with every gadget you could possibly imagine from a Crock Pot to a Waffle Maker! With Warm Wood Cabinetry & Custom Tile, preparing meals will feel like anything but a chore - and you can even take in Views while cooking. The huge Dining Table is perfect for family meals, or perhaps family game night!br br Sunset Bay Villa 209 has 3 spacious Bedrooms - all with large HD Flat Screen TVs and DVD Players. The breathtaking Master Bedroom sits Waterfront with access to the Balcony and of course those Views. With a comfy King Bed and Stunning Coastal Decor, it is paradise-found. Enjoy morning coffee in the Sitting Area, or slip out onto the Balcony while everyone still slumbers. The Master Bath features a Jetted Tub, Walk-in Shower with Double Sinks, and Double Vanity.br br Down the Hall, there are 2 more spacious Bedrooms - Bedroom 2 is simply adorable with a fun Whale Theme. There are 2 Twin Beds plus a Queen Sleeper here - just a great room for the kids. Each Bedroom and the Kitchen also have USB Charging Outlets, so keeping your charge is nice & easy! Bedroom 3 has a cozy Queen Bed and is also fully loaded. Full Bath 2 is conveniently located to both the Bedrooms and the Living Area, and has a Tub/Shower Combo. br br One of the most special things about Sunset Bay Villa 209 is that you get to bring the family dog along! Your furbaby will adore laying in the sun on the balcony and taking in that salty, sweet bay breeze.br br Sunset Bay Villa 209 - Remember, Memories made todgether, last a Lifetime!br br Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Friendly dogs welcome with $100 Pet Fee. Dogs MUST be current on Flea/Tick Preventative & Immunizations. No Cats. Every effort is made to ensure that all information and photographs in Seas

Condo

Sunset Bay Villa 209 by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$220.11

This is a 3 night minimum rental. Cozy cottage. Relax and enjoy! Walk the charming streets of Chincoteague! Walk to restaurants, shops and local activities. Artisan/ farmers market is less than one block away from the house! Every Wednesday and Saturday from April through October! Pick up pickleball courts nearby - both outdoor and indoor courts. Brianna’s playground park for the kids next door! Must try the red barbecue food truck within walking distance on Church Street. Pick up the trolley on Main Street and ride around to get a feel for the island! Dollar store, pharmacy, post office and grocery store are all easy walks from the house. Fitness lovers will enjoy the nearby pickle ball courts; outdoor basketball court; fitness equipment, picnic tables and soccer field across the parking lot.

Cottage

Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$182.99

This traditional style Chincoteague home has an eat-in kitchen, living space, a single bedroom downstairs, and two full-sized beds in an upstairs loft. There is one full bath that includes a washer and dryer. The home could sleep a family maximum of 6 (adults with children), or about 4 adults. The home has central air. Parking is available for two vehicles. The house is located close to Memorial Park (site of the annual pony swim) which has a playground for children, tennis courts, as well as free fishing for out-of-state residents who may not hold a fishing license. Minutes away from Assateague Island, enjoy sitting on the back porch after a long day at the beach. Rest comfortably inside this quaint little home!brbrPlease Note: NO Wifi or cable at this time!!

Perfect Chincoteague Home for your small family getaway

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$448.73

Amenities: Central Heating & A/C, W/D, Microwave, Dishwasher, Streaming TV Only , DVD, WiFi, Jacuzzi Tub, Waterfront Decks, Private Pier on Shallow Water, Outside Shower, Charcoal Grill. Linens and towels are provided. brbrFrom the first moment you step into this custom-built waterfront home you'll never want to leave! Offers sweeping views of Little Oyster Bay, large, covered veranda and private sundeck off upstairs main suite with Jacuzzi Tub. Downstairs offers 1st level owner suite with bathroom, nicely appointed living area and large kitchen leads out to waterfront deck. Upstairs you will find a lovely owner suite with full bathroom and jacuzzi tub. Office/BR (semi private) and 3rd level bedroom. Private dock for crabbing and fishing and don't forget your kayak! 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 King, 2 Queen, 1 Double FutonbrbrSaturday Change Overbrbr2026 Prime Season Rate $ 3003 per week ($ 429 per night) Weekly Rental Only July and August br2026 Off Season Rates $ 2303 per week $ 329 per night 3 night minimum brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Sunrise Over Little Oyster Bay - 4BR Waterfront home with decks & pier.

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$1034.7

Tie up your boat at our Deep Water Dock. Swim from the Dock!brbrEscape to this brilliant 4-bedroom Chincoteague retreat on Deep Hole Creek. With 2 king beds, 2 twin beds, and 5 full baths, this tranquil house offers the perfect space for guests to unwind. Enjoy the spacious great room -- living room - dining area and kitchen -- opening onto spacious decks with stupendous views across creeks, bays & marsh of Assateague and Oyster Bay. along with amenities like a washing machine, AC, heating, induction range and WiFi. Use our water toys (shared with Eureka!) and Fall in love with Chincoteague and enjoy the magic it has to offer.brbrBlair & Marthabrowners, Deep Hole Creek Vacation Rentalsbrmember. Chincoteague Chamber of Commerce

Epiphany-Deep Hole Creek-Chincoteague - Deep Water Dock! 2 King 4 Twin 5 Bath

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$388.58

4BR/2.5B***(Single Level Home) {1K, 1Q,2T, Bunk Q/T} Amenities: Central A/C, WiFi, Microwave, W/D, Dishwasher, hot tub, fireplace, electric grill, 2 decks, and a generator. brbrLovely home with canal views and dockage in Oyster Bay I. Large great room with fireplace, dining area leads out to deck and stocked kitchen with granite. This home has an elevator, hot tub, fenced in back yard, outside shower and lots to enjoy. Owner suite has it's own full bathroom with steam shower and water view deck. Great vacation home is new for the 2023 season. Jacuzzi tub. Property protected by outdoor security deposit on all three doors, front door, back deck and under carport directed at the entrance door. br brTHIS HOME DOES NOT PROVIDE LINENS AND TOWELS. PLEAE 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: 1K,1Q,2T, Bunk Q/TbrbrSunday Change OverbrbrSPECIAL LIMITED TIME: ANY REMAINING DAYS IN PRIME SEASON : $ 315 PER NIGHT / $ 2205 PER WEEK WITH 3 NIGHT MINIUM EXCLUDING JULY 26 TO AUGUST 2, 2026. BOOK NOW BEFORE OFFER ENDS. brbr2026 Prime Season Rate $ 2401 per week / 7 night minimumbr2026 Pony Swim Week $ 2856 per week / 7 night minimumbr2026 Off Season Rate $ 2401 per week / $ 480 per night with 3 night minimumbrbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

PonyTime - 4BR WATERFRONT home in Oyster Bay. Dock,decks,Hot Tub,NO LINENS

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$373.4

Pelican Sunset is a waterfront cottage on the Chincoteague channel. Enjoy beautiful sunsets, kayaking, and fishing from the dock. The house is clean, comfortable, relaxing, updated & decorated with original art from Hawaii, the Caribbean, and the Eastern Shore.brbrThe property is 4 miles from Assateague National Seashore Park and ½ block from where the Annual Assateague Pony round-up parades horses to the carnival grounds. The dock is also located in view of the NASA Wallops Island launch site.brbrPlease note: There are video cameras on the property which monitor the driveway, the dock, and the rear street entrance of the property lot. There are no cameras within the house.brbrPlease note: Pelican Sunset now offers the property with sheets and bath towels included for guests use.brbrThe space:brPelican Sunset has a dock for launching your kayak/canoe, fishing, crabbing, clamming, and sun bathing which extends into the Chincoteague Channel. There is a private deck outside the master bedroom which overlooks the southern Chincoteague channel. The enclosed front porch faces the waterfront/dock and the Chincoteague channel where fishing boats regularly come and go. There are two large screen wall mounted televisions, one in the downstairs den, and the other in the master bedroom. There is also a smaller television in the guest bedroom. The house is equipped with WiFi and television service for the main TV provided through a ROKU streaming device, a Blue Ray, and an antenna. The other two televisions have Blue Ray and antenna TV. Bedrooms are located on the second level and accessed by a spiral staircase. The master bedroom holds a king size bed, the guest bedroom holds a 54 double bed and 48 double bed. The downstairs den holds a queen sleeper sofa. The full bathroom, and half bathroom are located on the downstairs level. In addition, an outdoor shower is also available which is private, located behind the house, and is accessed by a brick walkway. The Pelican Sunset kitchen is renovated with a beautiful granite countertop and stainless steel sink, and fully stocked with pots and pans for cooking. The kitchen also is equipped with a gas range and oven, microwave, blender, juicer, toaster, and drip coffee maker. Because all island septic systems have limited capacity, Pelican Sunset provides a small washer and dryer for light laundry needs. The house has central Air Conditioning for guests comfort.brbrCome explore the Island, relax and enjoy the fantastic sunsets at Pelican Sunset!

Pelican Sunset - Waterfront With Pier

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$232.37

Welcome to Breezy Corner on our little slice of Heaven, Chincoteague Island. Located at the corner of Willow and Jester, you'll be tucked away in a quiet location in the heart of our Island, yet close to everywhere you want to be. The Attractions of Historic Main Street with so many quaint Shops and Restaurants, Robert Reed Waterfront Park, and the Chincoteague Carnival Grounds are just a short stroll or bike ride away. With 3 inviting Bedrooms and 1.5 Baths, this charming Home is ready to make your family's Vacation Dreams come true!brbrbrAfter a fun-filled day exploring Assateague National Seashore and searching for our Famous Wild Ponies, you'll love coming back to the comfort of a true home, not a hotel room, with all the comforts of home. Rinse off in the Outdoor Shower, and relax in the comfortable Living Room and enjoy Flat Screen Cable TV and Free WiFi. You’ll love the Historic Hardwood Floors throughout - so much character. Or sip Sweet Tea on the cozy Enclosed Porch, which lines the front of Breezy Corner, and take in that salty, sweet sea breeze.brbrBreezy Corner sleeps 7 in 3 Bedrooms plus a Den, without anyone ever feeling crowded. Just off the Living Area, Bedroom 1 has a comfy Queen Bed and is decorated with a cheerful Nautical Flair. The Jack and Jill Full Bath with Tub/Shower Combo, leads to the Den with a Sleeper Sofa and 2nd Flat Screen TV. The perfect place for the kids to enjoy their favorite movie and have a little down-time. Also on the 1st Floor is a Utility Room with a Full Size Washer and Dryer. There is also a convenient Half Bath located on the main floor.brbrWandering upstairs, you’ll find 2 more Bedrooms. Bedroom 2 is stunning in Colors of Sea Glass and has a Queen Bed, and Bedroom 3 is perfect for the kids with 2 Twins.brbrBook your time in Breezy Corner today for an easy-breezy Vacation you’ll never forget!brbrSeaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors. LINENS INCLUDED, NO SMOKING, NO VAPING, NO PETS. FAMILIES ONLY AND MUST BE AT LEAST 25.

Breezy Corner by Seaside Vacations & Sales

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$251.59

Experience classic Chincoteague Island charm with all the modern comforts at this lovingly updated waterfront home. Situated by Little Oyster Bay, the property features a private bulkhead boat dock perfect for crabbing, kayaking, boating, or simply enjoying peaceful waterfront moments.brbrInside, the home blends coastal charm with modern updates. A comfortable living room opens to the dining area, and classic kitchen creating a warm and inviting space for meals and gatherings. Two bedrooms, each with a queen bed, share a full hallway bathroom, making the home perfect for couples, small families, or friends traveling together.brbrRelaxation is easy at this home. The enclosed four-season porch offers a cozy spot to enjoy bay views in any weather, while the outdoor space features shade trees, a porch swing, and a covered grill area. From the yard, a short lane leads directly to the private dock, where you can launch a kayak, fish, or simply take in the serene bay setting. Keep an eye out for neighboring horses grazing nearby, adding a true Chincoteague Island experience.brbrOutdoor & Waterfront AmenitiesbrbrPrivate bulkhead boat dock for kayaking, crabbing, or boatingbrbrEnclosed four-season porch with waterfront viewsbrbrCovered grill area for outdoor diningbrbrYard with shade trees and porch swingbrbrShort lane to the dock for easy water accessbrbrOpportunity to spot Chincoteague’s famous horsesbrbrPrime Chincoteague LocationbrbrThis home offers a quiet waterfront retreat while remaining close to Chincoteague Island’s restaurants, shops, and attractions. A short drive brings you to Assateague Island for beaches, wildlife, and the famous wild ponies.brbrWhy Guests Love This HomebrbrClassic Chincoteague charm with modern updatesbrbrPrivate dock on Little Oyster Bay for boating and crabbingbrbrRelaxing four-season porch with scenic water viewsbrbrYard, grill area, and porch swing for outdoor enjoymentbrbrUnique opportunity to see horses from the propertybrbrYour Chincoteague EscapebrbrWhether you are kayaking, crabbing, grilling outdoors, or relaxing on the four-season porch, this home offers everything needed for a memorable Chincoteague Island waterfront vacation.

Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock

Chincoteague, Virginia, United States

Bed

1

Bath

Sleeps

$325.37

Escape to Lighthouse View, where breathtaking waterfront sunrises and iconic lighthouse views set the tone for your perfect Chincoteague getaway. This beautifully designed 2-bedroom, 2.5-bath townhome offers sweeping views of the Assateague Channel and the iconic Assateague Lighthouse, creating the perfect setting for a relaxing coastal getaway.brStart your mornings with breathtaking sunrises over the water and end your days unwinding on your private balcony as boats pass and wildlife drifts by. Thoughtfully decorated and superbly appointed, Lighthouse View blends comfort, style, and an unbeatable waterfront location.brbrThe SpacebrThe first level features a bright, open-concept floor plan ideal for gathering and entertaining. The living room, dining area, and fully equipped kitchen flow seamlessly together, all enhanced by natural light and scenic water views. A convenient half bathroom is also located on this level.brbrUpstairs, you’ll find two inviting bedrooms:brbrPrimary Suite: Queen bed, private bath, and a waterfront balcony overlooking the Assateague Channel and lighthouse—perfect for morning coffee or evening relaxation.brSecond Bedroom: Great for families, featuring a pyramid bunk (twin over full) plus an additional twin bed, with access to a full hallway bathroom.brbrWaterfront AmenitiesbrEnjoy everything that makes Chincoteague special right outside your door:brbrShared **deep-water boat dock** just steps awaybrUnobstructed views of Assateague Island and LighthousebrAbundant local wildlife, including birds, dolphins, and the famous wild ponies nearbybrIdeal location for boating, fishing, kayaking, and crabbingbrbrPrime LocationbrConveniently located near Chincoteague’s shops, restaurants, and bike paths, and just minutes from Assateague Island National Seashore, Lighthouse View offers easy access to beaches, nature trails, and outdoor adventures.brbrWhy Guests Love Lighthouse ViewbrbrIncredible waterfront and lighthouse viewsbrPrivate balcony off the primary suitebrBoat dock access for water activitiesbrComfortable, family-friendly layoutbrPeaceful yet close to local attractionsbrbrWhether you're seeking a peaceful retreat or an adventure-filled vacation, Lighthouse View is your perfect home base on Chincoteague Island.

Lighthouse View- 2BR | Waterfront | Boat Dock

Chincoteague, Virginia, United States

Bed

1

Bath