Vacation Home Rentals By Owner In Chincoteague, VA

Showing 140 Of 209 Vacation Rentals

$226.68

Seabright- Waterfront w/ Shared Deep Water Dock

Chincoteague, Virginia, United States

Seabright is a spacious three-story townhome on peaceful Marsh Island—just across the channel from Chincoteague and perfect for a relaxing getaway.brbrEnjoy crabbing and fishing from the community dock or have a waterfront picnic overlooking the channel and town.brbrInside, Seabright is newly renovated with stylish, comfortable décor. The main level features a bright living and dining area with a full wall of sliding doors that open to a large waterfront balcony—ideal for coffee, sunsets, or simply unwinding. A fully updated kitchen and half bath complete this floor.brbrThe second-floor waterfront bedroom offers a king bed and private balcony, with a shared full bath and laundry in the hall.brbrThe third-floor bedroom includes a queen bed and a versatile daybed (two twins or one king), plus its own private balcony—perfect for stargazing.brbrA modern, welcoming retreat with unbeatable water views and a tranquil island setting.

Bed

Bath

Sleeps

Exceptional(4)

$282.87

/ Nightly

Private Vacation Home

Sea Star- Waterfront w/ Boat Dock & Lighthouse Views

Chincoteague, Virginia, United States

Well-appointed townhouse with breathtaking sunrises over the Assateague Channel.brbrTake in spectacular views of the salt marshes, Assateague Lighthouse, and the famous wild ponies from the comfort of your home. Boat docking is right at your back door, making it easy to enjoy boating, kayaking, or crabbing at your convenience.brbrThe main level features a newly furnished living room with stunning water views and a seasonal gas fireplace. Beautiful hardwood floors flow throughout the open floor plan, which also includes a fully equipped kitchen, dining area, and a convenient half bath off the kitchen.brbrUpstairs, the waterfront master bedroom boasts a queen bed, private bath, and a balcony overlooking the channel, perfect for morning coffee or evening sunsets. The second bedroom has two twins and shares a full bathroom in the hallway.brbrA deep-water dock provides easy access to the bay and is ideal for crabbing, kayaking, or simply enjoying the peaceful waterfront setting. This townhouse offers the perfect combination of comfort, charm, and waterfront living for your Chincoteague getaway.

Bed

Bath

Sleeps

Exceptional(1)

$240.81

/ Nightly

Private Vacation Home

Miller’s Marsh- 2BR | Marsh Views | Shared Pier

Chincoteague, Virginia, United States

This charming home features exceptional decor and a peaceful natural setting. Guests have access to a shared crabbing pier on the inland creek.brbrThe first level includes an eat-in kitchen, living room, laundry area, and a convenient half bath. Both bedrooms are located on the second floor.brbrThe main bedroom has a queen bed and an adjoining full bathroom, with wetland views and sunsets from the private balcony. The second bedroom has two twin beds and its own private bathroom.

Bed

Bath

Sleeps

Exceptional(3)

$244.21

/ Nightly

Private Vacation Home

2 BR | Screened Porch | Walk to Town

Chincoteague, Virginia, United States

Miss Ida is brand-new construction, yet she beautifully evokes the charm of Chincoteague of yesteryear. A stunning blend of modern amenities and traditional styling provides extraordinary comfort, while the classic 1920s-inspired architecture and antique furnishings transport you to a bygone era.brbrThe queen bedroom includes a private half bath, and the second bedroom, with two twin beds, is conveniently located beside the full hallway bathroom.brbrEnjoy wonderful outdoor spaces on both the rear screened porch and the inviting front porch—perfect for relaxing after a day of island adventures.brbrFor larger groups, Miss Ida can also be rented together with the neighboring home, Myrtle on Mumford.

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Bath

Sleeps

$265.75

/ Nightly

Private Vacation Home

Lost Pearl- 4 BR | Fire Pit | Screened Porch

Chincoteague, Virginia, United States

Comfortable home situated on a quiet street, conveniently located close to town and Memorial Park. A great vacation home for everyone!brbrThe spacious screened porch overlooks a picnic area which features a grill and firepit—perfect for outdoor meals and relaxing evenings.brbrThe main bedroom offers a queen bed, cathedral ceiling, and private bath.brbrThree Additional Bedrooms:br• Two bedrooms with queen bedsbr• One bedroom with two twin bedsbrbrA second full bathroom is located in the hallway.

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Bath

Sleeps

$546.61

/ Nightly

Private Vacation Home

Sea Casa- Waterfront w/ Deep Water Dock & Fire Pit

Chincoteague, Virginia, United States

Fabulous sunsets and deep-water docking await at this comfortable and spacious home.brbrThe first floor features the main bedroom with a king bed, full bath, seasonal fireplace, and channel views. A second bedroom with a queen bed shares an adjoining hallway bath.brbrThe second floor offers a bright living room, fully equipped kitchen, and dining area. A half bath is also on this level, along with a large waterfront deck providing sensational views of the channel, bay, and stunning sunsets.brbrThe third floor includes a sleep loft with three twin beds—perfect for kids or extra guests.

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Bath

Sleeps

$203.27

/ Nightly

Private Vacation Home

Pony Swim Ridge- Waterviews, Close to Memorial Park

Chincoteague, Virginia, United States

Relax and take in stunning views of the Assateague Channel and Lighthouse from this charming two-story duplex. Fresh updates and all-new flooring make it bright and inviting.brbrThe first level features a living room, a fully equipped kitchen, a laundry area, and a half bath. Upstairs, both bedrooms share a hallway bathroom. The queen bedroom boasts a balcony with views of Assateague and the Lighthouse, while the second bedroom has two twin beds.

Bed

Bath

Sleeps

Exceptional(2)

$208.09

/ Nightly

Private Vacation Home

Vacation Diggs- 3BR | Screened Porch | Close to Park

Chincoteague, Virginia, United States

Close to Memorial Park for easy access to the boat and kayak launch, fishing, crabbing, and playgrounds, Vacation Diggs offers the perfect island getaway. The home features a large backyard and a relaxing screened-in porch—great for enjoying breezy evenings after a day on the water.brbrThe first-floor main bedroom includes a queen bed and a private full bath for added convenience.brbrUpstairs, the front bedroom features a full bed with a twin trundle, while the rear bedroom offers a queen bed. A shared full bathroom is located in the second-floor hallway.brbrA comfortable, well-located retreat—ideal for families, paddlers, and anyone ready to enjoy the best of Chincoteague.

Bed

Bath

Sleeps

Exceptional(2)

$210.65

/ Nightly

Private Vacation Home

Little Grit Cottage- 2BR | Walk to Town | Quiet Street

Chincoteague, Virginia, United States

Beautifully renovated, this traditional Chincoteague cottage sits in a quiet, natural setting with creek access. A small creek at the bottom of the backyard is perfect for crabbing and enjoying the surrounding nature.brbrThis one-level floor plan features a cheery kitchen, dining area, and a comfortable living room. Both bedrooms include queen beds and share a full hallway bathroom.brbrLittle Grit Cottage offers a tranquil setting with a spacious yard—great for children and outdoor relaxation. Despite its peaceful location, it’s just a short stroll to downtown stores, restaurants, and the waterfront park.

Bed

Bath

Sleeps

Exceptional(3)

$455.06

/ Nightly

Private Vacation Home

Sailer’s Rest- 4BR | Quiet Street | Walk to Town

Chincoteague, Virginia, United States

Beautifully renovated Chincoteague home in an in-town location, just a short walk to restaurants and shops. The owner offers a 10% Military Discount.brbrEnjoy great indoor and outdoor living spaces, including a fenced, landscaped yard and a comfortable deck with a gas grill. Relax and watch the world go by from the front screened porch.brbrThe first floor features a full kitchen, dining room, and living room, along with a convenient half bath.brbrThe second floor includes a bedroom with 2 twins on the right side, a bedroom with a pyramid bunk and a twin on the left side, and a second bedroom on the left with a queen bed. A large full bathroom is located at the end of the hallway.brbrThe third-floor bedroom features a king bed, private bath, and a spacious balcony.

Bed

Bath

Sleeps

Exceptional(1)

$395.67

/ Nightly

Private Vacation Home

Scooby Dunes- Waterview w/Shared Water Access

Chincoteague, Virginia, United States

This custom three-level home offers magnificent views of Oyster Bay and Miflin's Marsh from every room. Located in a quiet community perfect for walks, biking, and crabbing, Scooby Dunes features an outstanding floor plan with expansive marsh and bay views from the fabulous screened porch.brbrThe third level includes a great room, fully equipped kitchen, screened porch, deck, and a convenient half bath. The second level offers a large, comfortable living room ideal for gathering.brbrOn the first level, Bedroom One has a queen bed, and Bedroom Two has a twin-over-twin bunk plus an additional twin; these two bedrooms share a Jack & Jill full bathroom. Bedroom Three features a queen bed and private full bathroom, while Bedroom Four boasts a king bed with its own private full bathroom.brbrStep outside and take a stroll to the end of the lane to crab from the bulkheaded shoreline of Oyster Bay.

Bed

Bath

Sleeps

Exceptional(32)

$273.38

/ Nightly

Private Vacation Home

Pony Swim - Water Front Duplex,beautiful views. decks,NO LINENS PROVIDED

Chincoteague, Virginia, United States

Amenities: Central A/C, Dish TV, VCR, Microwave, Dishwasher, Keurig, W/D, WiFi, Decks, DOCK for 2025brbrWaterfront duplex located on East Side Drive. This beautiful property has a with great views of Assateague Island and the Lighthouse. Newly remodeled kitchen, living room, and dining room. Kitchen is open to the dining room, perfect for entertaining while you cook! Dock is ready for 2025.. Great views and Memorial Park just around the corner to fish and crab.br brTHIS 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 Queen, 4 TwinsbrbrSaturday Change Overbrbr2026 Rates $ 1456 per week/ $ 208 per night ( 3 night min. ) brbr**** If paying with a Debit or Credit Card, there is a 3% Convenience Fee in addition to the charge. ****

Bed

Bath

Sleeps

Exceptional(16)

$178.57

/ Nightly

Private Vacation Home

Ocean House - duplex -1st level bedroom. Deck, NO LINENS PROVIDED

Chincoteague, Virginia, United States

Amenities: Central A/C, Microwave, Dishwasher, W/D, Cable TV, VCR, WiFi, ChromeCast, Propane Grill, Firepit, Outside Shower, DeckbrbrBright and spacious duplex located on private lane. In walking distance of many island attractions. Offers second floor master bedroom suite. 1 bedroom and 1 bath downstairs/1 bedroom and 1 bath upstairs. Offering WiFi.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).brbrbrBed Sizes: 1 Queen, 1 Double, 1 Twin Sleep Sofa, 1 Queen Sleep SofabrbrSunday Change Overbrbr2026 Prime Season Rate: $ 980 per week $ 140 PER NIGHT ( 3 night min.) br2026 Off Season Rate: $ 784 per week $ 112 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. ****

Bed

Bath

Sleeps

Exceptional(20)

$218.58

/ Nightly

Private Vacation Home

Blue Water - Single Family Home - In Town - LG. FENCEED IN YARD, NO LINENS

Chincoteague, Virginia, United States

Amenities: Central A/C, Microwave, W/D, Dishwasher, Keurig, WiFi, Cable, TV, Deck, Gas Grill, Large Fenced in Back YardbrbrWalk to everything including shopping, restaurants and entertainment from this convenient in town location! This house has been completely renovated and is a great house for your vacation, with large fenced in back yard. Blue Water has a large kitchen, open to the dining room, perfect for everyone to spend time together. Off the living room is a separate room which can be closed off for even more privacy. This home is protected by an outside surveillance system located on the front door facing the street. brTHIS 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).brbrbrBed Sizes: 2 Queens, 2 Twins, 1 Double Sleep SofabrbrSaturday Change Overbrbr2026 Rate Prime Season: $ 1351 per week / $ 193 per night with 3 night minimumbr2026 Rate Off Season: $ 1050 per week / $ 150 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

Bath

Sleeps

$203.08

/ Nightly

Private Vacation Home

Teal Away- Amazing Views, Kayaks, Shared Pier

Chincoteague, Virginia, United States

Teal Away is thoughtfully equipped and beautifully decorated for your vacation comfort. Relax on the deck or balcony while enjoying views of the marsh and creek, and take in spectacular sunrises each morning.brbrGuests have access to a shared pier directly on the creek, perfect for crabbing and kayaking. Two kayaks are included with the rental. The location is just a short walk to shops, restaurants, food trucks, and outdoor activities.brbrThe main floor features a comfortable living room, a half bath, and an eat-in kitchen. Both bedrooms are located on the second level. The front bedroom offers a king bed, private full bath, and a private balcony with views of the Assateague Channel. The rear bedroom has two twin beds, a private full bath, and its own balcony.brbrTeal Away combines peaceful waterside living with easy access to all the charm and amenities of Chincoteague.

Bed

Bath

Sleeps

Exceptional(1)

$256.1

/ Nightly

Private Vacation Home

The View-Waterfront w/ Shared Crabbing Pier

Chincoteague, Virginia, United States

Newly Renovated Waterfront Property with breathtaking views of the brAssateague Lighthouse and Assateague Island. The Assateague Channel is teeming with waterfowl and wildlife, making this a true birdwatchers paradise. Enjoy spectacular sunrises and sunsets from three private balconies.brbrThe brand-new kitchen features warm tones and modern finishes, counter seating, new appliances with ice maker, a filtered water system at the faucet, and updated flooring throughout main level. A freshly painted interior and a new dining area seating six create a bright, welcoming space for meals and gathering. New central air and heating.brbrWide new sliding glass doors open to spacious waterfront balconies, extending indoor-outdoor living. Thoughtfully chosen natural coastal finishes reflect the surrounding water and marsh, bringing the serenity of the outdoors inside.brbrA rear den with a queen sleeper, new half bath, and workspace offers a third semi-private sleeping area and opens to a third private deck with a new large gas grill.brbrUpstairs, you will find two inviting bedrooms, each with its own private bathroom. The waterfront king suite offers sweeping views and a private waterfront balcony, perfect for morning coffee or quiet relaxation. The second bedroom features a queen bed and a king trundle bed, providing flexible sleeping arrangements for families or friends.brbrFor outdoor enjoyment, the property features an extra large outdoor shower and access to three shared piers, perfect for crabbing and taking in the peaceful surroundings. A designated community kayak launch pad is available.

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Bath

Sleeps

$248.54

/ Nightly

Private Vacation Home

Sailer Moon- 4 BR | Walk to Town | Sunset Views

Chincoteague, Virginia, United States

Renovated Victorian home offering beautiful views of the Chincoteague Channel and stunning sunsets from the balcony. A screened porch with picnic table is located off the kitchen at the rear of the house. Wade across the makeshift boardwalk to a private shelled beach area, perfect for launching kayaks or enjoying the evening sunset.brbrThe second floor features three bedrooms. One queen bedroom with balcony access and a bedroom with two twins share an adjoining full bath. The third queen bedroom also has balcony access with water and sunset views.brbrA spacious third-floor loft provides a comfortable and private fourth sleeping area, featuring a double bed, TV, sitting area, and half bath. A second full bathroom is located on the first floor.

Bed

Bath

Sleeps

$320.7

/ Nightly

Private Vacation Home

Tiki Time- Canalfront w/ Boat Dock & Tiki Bar

Chincoteague, Virginia, United States

Great outdoor living awaits at Tiki Time! A private boat dock, Tiki bar, and large screened porch create the perfect setting for relaxing, crabbing, and enjoying time by the water.brbrInside, the home is comfortable and welcoming. The main bedroom features a king bed and private bath. The second bedroom offers two sets of bunks, and the third bedroom has two twin beds. A shared full bath is located in the hallway for convenience.brbrAfter a fun-filled day on the island, gather in the spacious screened porch for evening meals, games, or simply unwinding. The Tiki bar sits right along the canal—an ideal spot for sipping a drink and soaking up the waterfront atmosphere.

Bed

Bath

Sleeps

$353.32

/ Nightly

Private Vacation Home

Tin Cup Palace- Community Boat Launch, Fire Pit & Screened Porch

Chincoteague, Virginia, United States

Architect-designed, Tin Cup Palace blends contemporary lines with a mid-century modern flair. Vaulted ceilings and an open floor plan create a bright, airy feel throughout.brbrSet in a serene, beautifully landscaped location, this home offers true peace and quiet. Enjoy morning bird songs from the screened porch and end your day stargazing from the front deck. The screened porch, tucked among tall pines, is an especially lovely spot to relax.brbrThe main bedroom features a king bed and private bath. The second bedroom has a twin-over-twin bunk bed, while the third bedroom includes a queen bed and a 32-inch flat-screen TV. A shared full bath is located in the hallway.brbrOutdoors, a firepit with a ready woodpile invites evening gatherings—just bring your marshmallows!

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Bath

Sleeps

$364.82

/ Nightly

Private Vacation Home

Topaz- Canalfront with Boat Dock

Chincoteague, Virginia, United States

A great island getaway, Topaz offers spacious decks, a private boat dock, and a quiet setting in the desirable Oyster Bay community.brbrThis elevated home provides expansive deck space, plus a charming widow’s walk that offers a peek of the bay. A screened porch with a picnic table sits beneath the house—perfect for shaded outdoor dining.brbrTopaz also includes a private boat dock on the canal, giving you quick access to beautiful Oyster Bay for boating, kayaking, and crabbing.brbrInside, the main bedroom features a queen bed, deck access, and a private full bath. The second bedroom has two twin beds. The third bedroom includes a queen bed, and the fourth bedroom has two twin beds — and these two bedrooms share the adjoining hall bath.brbrA peaceful coastal retreat with plenty of space for family and friends to enjoy the island.

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Rent a place that suits your needs

Cottage

View 25 Cottage

Private vacation home

View 194 Private vacation home

Most popular vacation rentals in Chincoteague

$587.78

/ Nightly

Private vacation home

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$467.77

/ Nightly

Private vacation home

Stunning home in Sibenik

Sibenik, Sibenik-Knin, Croatia

Bed

Bath

Sleeps

$468.43

/ Nightly

Private vacation home

Kingslanding- 4BR | Canalfront | Screened Porch

Chincoteague, Virginia, United States

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Bath

Sleeps

$473.07

/ Nightly

Private vacation home

2 Mi to Downtown: Tranquil Abode in Chincoteague!

Chincoteague, Virginia, United States

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Bath

Sleeps

$481.96

/ Nightly

Private vacation home

Misty Manor! Updated Cottage Near Beach! Water Access, Linens Included!

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$494.12

/ Nightly

Private vacation home

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$500.30

/ Nightly

Cottage

COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$505.54

/ Nightly

Condo

Sunset Bay Villa #315- Waterfront Condo w/ Pool & Gym

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

$576.21

/ Nightly

Private vacation home

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

Chincoteague, Virginia, United States

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Bath

Sleeps

$1034.70

/ Nightly

Private vacation home

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

Chincoteague, Virginia, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Chincoteague, VA

$226.68

$282.87

$240.81

$244.21

$265.75

$546.61

$203.27

$208.09

$210.65

$455.06

$395.67

$273.38

$178.57

$218.58

$203.08

$256.1

$248.54

$320.7

$353.32

$364.82

Rent a place that suits your needs

Most popular vacation rentals in Chincoteague

$587.78

$467.77

$468.43

$473.07

$481.96

$494.12

$500.30

$505.54

$576.21

$1034.70

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