Home Vacation Rentals By Owner In Chincoteague, VA

Showing 140 Of 262 Vacation Rentals
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Exceptional(38)

$149.1

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Private Vacation Home

Cattail Cottage -Allergy Friendly Home -In Town-LINENS & TOWELS PROVIDED

Chincoteague, Virginia, United States

Amenities: Central A/C, Cable TV, Microwave, WiFi, Deck, Charcoal Grill, Washer and Dryer. Hypoallergenic linens, towels provided, all pillows (bed pillows and decorative pillows), tissues and toilet paperbrbrCharming Cottage located on a quiet private lane. A great in town location. Perfect for walking or biking to Main Street and Maddox Blvd. activities, shops and eateries. A short drive to the beach and marina areas. This home will pleasantly surprise you! New owner has Carbon coconut filter on ceiling fan in bonus room, portable air purifier and plug-in CLARiiON air purifiers. Offering a large deck, and grill and spacious sunroom to relax and enjoy your visit. With this house as well as beach chairs and an umbrella. Hypoallergenic linens, towels provided, all pillows (bed pillows and decorative pillows), tissues and toilet paper. 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).brbrLINENS AND TOWELS PROVIDEDbrBed Sizes: 1 King, 1 Queen Sleep Sofa, FutonbrbrSaturday Change Overbrbr2026 Off Season Rates $ 100 per night / $ 700 per weekbr2026 Prime Season Rates $ 115 per night / $ 800 per weekbr2026 Pony Swim Week $ 122 per night / $ 850 per week brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****
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Bath 2

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Sleep 5

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Exceptional(18)

$170.95

/ Nightly
Private Vacation Home

Assateague Lookout - Water Front townhome W/view. - Shared Pier, No Linens

Chincoteague, Virginia, United States

Amenities: Central A/C, W/D, WiFi, Microwave, TV, DVD, STREAMING TV ONLY , Fireplace, Screen Porch, Dishwasher, Deck, Gas Grill, Shared Pier, Outside Shower. New Walk-In Shower in main bedroom suite. brbrVery nice waterfront townhouse with remodeled chef's kitchen. Spectacular vistas of Assateague Island. Relax on the screened porch and enjoy the water view and the lighthouse. Dining room has a fireplace and is open to the kitchen and living room. Upstairs, the master bedroom has large walk-in closet and private bathroom with new Walk-In Shower. Perfect spot for kayaking . 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). brbrThis home does not provide linens and towels. Please bring your own or call us to rent them.brbrbrBed Sizes: 1 Queen, 2 Twins, 1 FutonbrbrSunday Change Over Prime season allowing 3 night minimum w/guest paying cleaning fee.brbr2026 Rate Prime Season: $ 1001 per week / $ 143 per night with 3 night minimumbr2026 Rate Off Season: $ 805 per week / $ 115 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. ****
Bed 2

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Bath 2

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Sleep 6

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Exceptional(1)

$266.58

/ Nightly
Private Vacation Home

Allowaves- Luxury Town Home with Community Pool & Fishing Pier

Chincoteague, Virginia, United States

Allowaves is a welcoming coastal-style townhome on Chincoteague Island, designed for easygoing island living and time well spent together. With bright interiors, breezy coastal touches, and multiple outdoor spaces, this home captures the relaxed rhythm of the shore. Guests also enjoy access to a community swimming pool and fishing pier, ideal for slow mornings and sunset views over the water.brbrThe three-level layout offers both togetherness and privacy. The first floor features two comfortable bedrooms, a full hallway bath, and a cozy sitting nook—perfect for kids, games, or a quiet place to unwind. The second floor serves as the heart of the home, with an open kitchen, dining area, and living space that make sharing meals and conversation easy. Step out onto the deck to enjoy coastal breezes and casual outdoor dining. The top floor is a private retreat, featuring a spacious bedroom with its own bathroom and balcony—an ideal spot to enjoy peaceful mornings or island sunsets.brbrOutside, the covered carport is set up for relaxed coastal evenings with seating, a grill, and a picnic table—great for post-beach dinners and laid-back gatherings. Whether you’re returning from the beach, heading out on the water, or exploring nearby wildlife areas and island favorites, Allowaves offers a comfortable, coastal home base perfectly suited for families and friends enjoying Chincoteague’s natural beauty.
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Sleep 9

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Exceptional(1)

$576.21

/ Nightly
Private Vacation Home

Above The Bay - SFH - WF w/Views Everywhere. Brand New Home, Linens included

Chincoteague, Virginia, United States

Amenities: Central A/C, WiFi, Microwave, W/D, TV. NO PETS AND NO SMOKING. brbrLIMITED TIME SPECIAL: Book any remaining weeks for Summer 2026 at $ 3500 per week plus tax and fees (Pony Swim Week 07/25-08/01/26 Excluded) . Book now this offer won't last long. brbr Dynamic Waterfront home with outstanding unobstructed views of Assateague Island, with this very spacious and lovely well-appointed rooms. Open & covered decks (each level) so you can enjoy the view in any weather. First level offers living area, bathroom and 2 bedrooms. Leads out to waterfront deck. Top area is large open great room, owner's suite with full bathroom and bathroom off of kitchen area. Great waterfront decks to enjoy the views. Coffee Bar at each level. 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).brbr***This property requires BOTH the $600 Refundable Security Deposit and the $70 Non Refundable Security Protection Plan when renting.***brbrBed Sizes: brSaturday Change OverbrbrLIMITED TIME SPECIAL: Book any remaining weeks for Summer 2026 at $ 3500 per week plus tax and fees ( Pony Swim Week 07/25-08/01/26 Excluded). Book now this offer won't last long. brbr2026 Prime Season Rate $ 4000 per week brbr2026 Off Season Rate $ 3206 per week brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****
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Bath 2

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Sleep 8

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Exceptional(6)

$473.27

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Private Vacation Home

Family Oasis Handicap accessible and Dog friendly

Chincoteague, Virginia, United States

This home is very close to Historic Main Street, close to shops, restaurants, and local attractions, just minutes away from Maddox Blvd. You will be in the middle of the best of the island. This house is perfect for a large family or group of friends. It provides plenty of parking for your cars, boats, or any other vacation necessities! It is handicap accessible with a ramp leading to the back entrance. There is also a large fenced in area that your pup will have plenty of room to run around!brbrWelcome to Family Oasis! This 4 bedroom, 3 bathroom house is pet friendly and newly renovated! When you book this rental you may fall in love with the cozy, beachy aesthetic before you realize its prime location! But when you do, you'll notice it is centrally located on Ocean Blva. This home is very close to Historic Main Street, close to shops, restaurants, and local attractions but also just minutes away from Maddox Blvd. You will be in the middle of the best of the island! Immerse yourself in a relaxed state of mind in this beautifully decorated home with modern amenities. This house is perfect for a large family or group of friends. It provides plenty of parking for your cars, boats, or any other vacation necessities! It is handicap accessible with a ramp leading to the back entrance. There is also a large fenced in area that your pup will have plenty of room to run around!brbrThe main level of this home features a cozy seating area as you enter through the front door. It is surrounded by windows- the perfect spot to sip your morning coffee and enjoy the sunshine! Making your way into the living room, your whole group can easily hang out together on comfortable furnishings and watch a movie on the flat-screen TV. The kitchen is fully equipped and has everything you will need to whip up your meals. The dining area has seating for seven, and you can find extra seating at the barrel bar in the nearby kitchen. Located through the kitchen, there is a washer and dryer and a full bathroom that has a handicap accessible shower. This floor also features 2 bedrooms. The first bedroom has two twin beds where there are fun video games and a TV. The second bedroom has a king bed and a smart TV. There is another full bathroom with a shower/tub combo! Heading up the stairs, there are two more bedrooms. The first bedroom has a queen bed and around the corner there is a twin trundle bed with a large smart TV.brThe second bedroom also has a queen bed. This floor also has a full bathroom with a stand up shower.brLinens available upon request.brbrOutside, there is a spacious backyard that is fenced in -perfect to let your dog run around! This is the best location for enjoying the night breeze and sitting around the fire pit in the colorful adirondack chairs. Take advantage of the outside shower that makes it easy to rinse off the sand after a fun day at the beach! Head up on the porch and you can enjoy sitting on the comfy furniture while you cook on the brand new propane grill!brbrFamily Oasis wants this to be the most relaxing vacation you can imagine. brbrAdditional features of this house include 4 bedrooms, 3 full sized bathrooms, washer/dryer, dishwasher, fully equipped kitchen, beach chairs, coolers, central AC and heat, lots of family games, smart TVs, WIFI, large back deck, fire pit, yard toys, outside shower, and a large fenced in yard. PET FRIENDLY. Accommodates 10.br
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Sleep 10

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$477.84

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Cottage

Cozy island cottage with a Key West flair - CLOSEST TO THE BEACH!!!

Chincoteague, Virginia, United States

Every room of this island cottage has been updated and furnished with fresh fixtures, furniture and decor in a relaxed, comfy coastal style. brbrClean and well appointed, from the granite counter tops and stainless appliances in the kitchen to the new queen and twin sets in the charming bedrooms. Every detail of this island home was carefully considered to ensure your visit is relaxing and comfortable.brbrThe wide and inviting front porch is the first thing you will notice as we welcome you to our island haven. Beyond the front door, you will find an open living room and kitchen designed for easy entertaining with plenty of seating and views through to the spacious screened porch. Eat in the kitchen or gather around the dining area on the screened porch. brbrNestled in the back are two bedrooms; one with a queen and another with two twin beds. Both bedrooms feature smart flat screen TV's. All quality linens and hotel style towels are provided. brbrThe tiled bathroom includes a roomy waterfall shower, as well as, a full sized washer and dryer. brbrIn addition, this coastal retreat has central air, wireless internet and smart TV's in the living room and both bedrooms. brbrTucked away in the closest neighborhood to the Assateague National Seashore, this quiet street is only a few minutes to the beach, bike rentals, restaurants and shopping. Rental includes access to the community boat launch.
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Exceptional(29)

$2954.9

/ Nightly
Private Vacation Home

Eureka! on Deep Hole Creek - Waterfront! Sleeps 16

Chincoteague, Virginia, United States

Eureka! is the PREMIER vacation home on Chincoteague. Period. 'Spectacular' and 'Fantastic' are the words that come to mind when you consider the design of the house and its location. Our aim is that each guest also uses those words to describe their entire vacation experience.brbrSpecials available at: Deep Hole Creek Vacation Rentals: Member, Chincoteague Chamber of Commercebr brThe siting of this house is unique: You are above the 'Deep Hole' at the end of Deep Hole Creek, overlooking Oyster Bay, Little Oyster Bay, Assateague Bay with vast unobstructed natural water views.brSummer rentals are full weeks only, Saturday to Saturday. Fall and Spring rentals are usually mid-week to mid-week.brbrNo Smoking and No Pets, Please! Thank you for not smoking anywhere on the property, and please do not bring fireworks.brbrElevator in Main House! A 2nd Refrigerator for all your food & drink.brWith one bathroom designed to be handicapped accessible, we are very accommodating for people in wheelchairs or who have a hard time with stairs. brThe elevator is serviced and inspected twice a year by the same tech from Delaware Elevator. For safety reasons, we ask that children not be allowed to use it unattended.brbrThe handicapped bathroom (in one of the king bedrooms) has a fully tiled floor with continuous access so a wheelchair can easily be moved into the shower area. There are also six hand grips in essential spots.brThe elevator has the following dimensions:br 1). The opening in the elevator door when the accordion door is fully open: 33 inchesbr 2). The depth of the elevator cab- 41 inchesbr 3). The width of the elevator cab- 42 1/2 inchesbrbrMain House: Sleeps 10:brOn the first level, with 9' ceilings, there are FOUR bedrooms, each with its own bath, and each with its own private balcony. All have water views. Two have water views in two directions. ONE Bedroom, designed for kids, has 4 bunk beds (3 twin, 1 full) but could handle single adults if needed. brTHREE BEDROOMS have KING beds. Each of the king bedrooms has custom tiled showers. One is handicapped accessible, another has a marble vanity, the third has a custom glass vanity.br Media Room: a full size Sleep Sofa.brThe Guest House: brSleeps 6.brGuest House - First Floor: Sleeps 2 (King bed).brGuest House - Second Floor: Sleeps 4 (two rooms, one with a sleep sofa, the other with two twin beds).brThere are no cooking facilities in the Guest House. It is never rented separately.brbrNo other house on Chincoteague can legally accommodate nearly as many people. brFantastic for Large Family Reunions: When rented in conjunction with 2 neighboring houses, 28 people can be accommodated on site. Ask for details!brLarge groups hosted (in conjunction with adjacent rental houses) include weddings, corporate retreats, a yoga weekend, a hunting retreat, and a quilter's bee.brOver 100 feet of frontage on Deep Hole Creek -- the pictures do not do it justice! (Well, the video comes closer!) brThe 2nd floor deck offers the most sweeping & spectacular views from any house in Chincoteague... brAt ground level, there are expansive wood decks, and a long bulkhead for crabbing and tying up boats and plenty of sun or shade (with seating and dining areas) depending on your preference. Hammocks. Plus several shaded picnic table and seating areas. br And a floating dock that makes water access even easier! The floating dock is shared with Epiphany (a neighboring house), as are the water toys, which include a Canoe, two 2-person Kayaks, and two Stand-up-paddle boards.brThere is an open breezeway deck with stairs down to the dock area as well as indoor stairs. brOn the second floor, you enter directly into a large Great Room and Kitchen with cathedral ceilings, bay windows, picture windows, two large decks (one with the wide-angle view and full sun; the other covered with an outdoor grill); both have dining areas. brThe kitchen is simply fabulous: Look at the photos, and read the details below.brThere is also a cozy media room with a 50 flat screen TV and a full size sleep sofa. The 2nd floor bath is next door, so using this room for sleeping is attractive. Enjoy our large library of books. Many guests have commented on how much they appreciate our large collection of board games.brBroadband Charter/Spectrum Internet/Wi-Fi. brbrTwo decks open off the 2nd floor great room. One is the open deck with the wide angle views, the other is the covered breezeway deck, still with great views, but also with the gas grill. Both decks have dining tables. brbrGuest House, First Floor Suite (First floor of small house): Across the breezeway (cedar-shingled exterior, radial, almost two story window wall, on the left in the aerial photo). All on the main floor, the living area has sweeping water views through the stunning curved window wall. The Primary bedroom (king bed), boasts a LUXURIOUS bathroom with a TILED two-person shower with body jets. THERE IS a WONDERFULLY private corner WATERFRONT balcony looking south. brbrThe primary suite in the guest house is an ideal choice for the special couple... whether you are planning a Chincoteague Wedding, a Golden Anniversary, or anything in between. Email for more details..brThe 2nd floor of the Guest House has two additional rooms: One is right over the creek with the best view of all, with a sleep sofa. This is the best room on a mid-winter sunny afternoon. The other has two twin beds. Both rooms share a bath. Use of these rooms increases the capacity of the house to 16. brExtensive ground level wooden decks all along the bulkhead, hammocks, lots of deck furniture provide many spaces for relaxation.brThe ladder down the side of the bulkhead to the floating dock makes boating and swimming easier. Bring water shoes!brNOTES: if you bring small children the waterside dock areas will require you to exercise constant vigilance over them. The upper decks offer more enclosed outdoor areas. Some people with small children choose not to use this house for that reason. We understand, and hope you will return when the kids are a bit older.brAll rentals include Bedlinens (Sheets only) Please bring your own towels and beach towels.brKeywords: Chincoteague Island Vacation Rental, Chincoteague, VA. Has views of Assateague, marsh and bays, Sleeps 16, 7 baths, Internet, Has Multiple Decks, Floating Dock, Catch Crabs, Swim, and Boat from the House, See the Chincoteague Ponies!brTwo Miles from the bridge to Chincoteague National Wildlife Refuge on Assateague. Pony Penning 2024. Family Reunions, Elevatorbr
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Bath 7

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Sleep 16

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Exceptional(18)

Select Dates for Price
Private Vacation Home

Blarney Shores -Waterfront -Pet Friendly - Balconies , No Linens Provided

Chincoteague, Virginia, United States

Amenities: Central A/C, W/D, Microwave, 5 TVs, DVD, Dishwasher, WiFi, Deck/Patio, Balconies, Gas Grill, Gas Fireplace, Keurig and New Dock for 2022.brbrContemporary 4 bedroom 3 bath Waterfront home. Pet friendly, located in a private area off North Main Street. Offers 2 master suites with waterfront balconies. This home does not disappoint with its vaulted ceilings and gas fireplace. Offers a well-equipped kitchen with stainless steel appliances. Keurig Coffee Maker. Garage access to store all your beach equipment, bikes & kayaks.br br Pet friendly home $75.00 (per pet) fee will be added to your reservation. This home does not provide linens and towels. Please bring your own or call us to rent them. This Property accepts Dogs Only (limit 2)brbrGarage Access to store beach supplies/kayaks***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 Queens, 2 Twins, 1 Twin w/ TrundlebrbrSunday Change Overbrbr2026 Prime Season Rate $ 2415 weekly rental only brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****
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Bath 3

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Sleep 8

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Exceptional(32)

$181.22

/ Nightly
Private Vacation Home

Hancock House -Single Family Home - Screened Porch, NO LINENS PROVIDED

Chincoteague, Virginia, United States

Amenities: Central A/C, Dishwasher, Microwave, W/D, TV, Cable, Outside Shower, Screened Porch, Open Porch, WiFi, Electric GrillbrbrThis historic island home is immaculate! Tucked away on a private lane with a large, screened porch overlooking a lovely yard. A perfect spot to unwind and enjoy your beach vacation! Remodeled kitchen and bath, new laundry room, spacious living room and open front porch with distant views of Oyster Bay. brbrNO LINENS AND TOWELS ARE PROVIDED SO BRING YOUR OWN OR CALL US TO RENT THEM.brbrCancellations made 30 days prior to arrival will receive 100% of refund  of all monies minus $ 39 Processing Fee and Any Credit Card Convenience Fees Paid.  If less, then 30 days: the advanced rent is only refundable subject to the following: The property is re-rented for the same period. Re-rental of less than a full week will be refunded on a pro-rated basis. The Agent will retain a $39.00 processing charge, and any convenience fees charged. *Deposits are not refunded for ANY reason (including bad weather).brbrbrBed Sizes: 1 Queen, 1 Double, 1 TwinbrbrSaturday Change Overbrbr2026 Prime Season Rates $ 1225 per week br2026 Off Season Rates $ 875 per week / $ 125 per night 3-night min.brbrbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****
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