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Holiday rentals in Chincoteague

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Quick stats about holiday rentals in Chincoteague

  • Total holiday rentals

    Explore 670 holiday rentals in Chincoteague

  • Nightly prices starting at

    Chincoteague holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 16,760 verified reviews to help you choose

  • Family-friendly holiday rentals

    580 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 210 rentals that welcome pets

  • Holiday rentals with a pool

    140 properties feature pools

  • Rentals with dedicated workspaces

    490 properties have a dedicated workspace

  • Wifi availability

    660 of Chincoteague holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Free parking on premises across Chincoteague rentals

  • 4.8 Average rating

    Chincoteague stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Chincoteague

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A cozy cottage exterior is presented with a light blue façade and a welcoming front porch. The entrance features a small overhang and steps leading to the front door, accompanied by neatly trimmed bushes and a well-maintained lawn under clear blue skies.
Cottage in Chincoteague
4.94 out of 5 average rating, 208 reviews

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

ValueFamilyLaundry

Top guest favourite
Home in Chincoteague
4.96 out of 5 average rating, 105 reviews

Island House: Kayaks, Bikes, Beach Gear & Firepit

Welcome to Happy Ours! Relax with the whole family at this peaceful Chincoteague home. Walk to the park (Pony Swim!). This beachy cottage offers all the charm with plenty of space, in a quiet area with a huge property. This is a family home that we enjoy with friends & family year-round. We would love to share that experience with you! If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Chincoteague has to offer!

LocationFamilyBack garden

Top guest favourite
The exterior of a charming white cottage is showcased, featuring two sets of stairs leading to the front porch. The well-maintained lawn is punctuated by a small garden area, and a decorative figure can be seen near the entrance.
Cottage in Chincoteague
4.95 out of 5 average rating, 64 reviews

Waterfowl Watch Chincoteague & bikes Fall dates

Small family-friendly two bedroom cottage in a quiet area with a slight view of Little Oyster Bay. 1 mile to Maddox Blvd/ 3 miles to Assateague Is. A queen,bunk beds w/trundle & sleeper sofa. Private back yard, property is cute & clean, it is a beach cottage not a luxury resort. Get back to nature or explore many shops and activities. Fire pit,outdoor seating,charcoal grill, backyard games, Bikes(waiver required). Rental kayak service available year round. Jan-March monthly is avail inquire

ValueLocationCheck-in

Top guest favourite
Adirondack chairs are arranged in a semicircle facing a stunning sunset over Chincoteague Bay. The sky reflects hues of orange and pink, while the calm waters mirror the colors above. A firepit is positioned nearby, surrounded by tall grasses.
Cottage in Chincoteague
4.96 out of 5 average rating, 168 reviews

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

FamilyLocationWalkability

Top guest favourite
A coastal retreat is presented in a light-colored two-story home elevated on stilts. A set of steps leads to a covered porch with a railing. A small seating area with yellow chairs is visible beneath the porch. Lush green trees surround the property.
Home in Chincoteague
4.98 out of 5 average rating, 120 reviews

Pearl in the Pines: bikes, kayaks, EV charger

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.

ValueLocationQuiet

Top guest favourite
The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.
Townhouse in Ocean City
4.97 out of 5 average rating, 536 reviews

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

LocationValueCleanliness

Top guest favourite
A light-filled living room is presented with soft beige seating arranged around a round, patterned coffee table. A landscape artwork adorns the wall above the couch. Natural light streams through a nearby window, highlighting a plant tucked in the corner.
Home in Chincoteague
4.94 out of 5 average rating, 204 reviews

Adorable Beach Cottage Just Steps From Town & Bay

Escape to Wiggle Bay, a darling 1955 2 BR sunny cottage nestled in the heart of "one of the most beautiful, charming small towns in Virginia." Enjoy a bay breeze on the screened front porch--heaven! Perfectly located on a quiet street, just steps from local shops, a coffee house, and the waterfront park, where you can watch the boats, enjoy the sunset and feed the ducks. Just 2.3 mi to Assateague Seashore/Chincoteague Refuge. Ideal for a peaceful and convenient getaway!

ValueFamilyWalkability

Top guest favourite
A charming coastal home features a light blue front door and large windows adorned with greenery. Stone accents and a gabled roof complement the inviting appearance. A well-maintained lawn with potted plants and garden decorations surrounds the house, enhancing its welcoming atmosphere.
Home in Chincoteague
4.98 out of 5 average rating, 84 reviews

cozy sunset cottage

Feel at home as soon as you walk in. Indulge in a coastal retreat that embraces you with a beach-inspired ambiance from the moment you arrive. Experience the carefree comfort of this centrally-located home, thoughtfully designed to exude a beach-like charm. And don't miss the special touch—an inviting screened-in outdoor lounge area where you can relax, unwind, and soak up the coastal vibes, creating cherished moments reminiscent of blissful days by the shore.

FamilyLocationIndoor spaces

Guest favourite
A cozy bedroom features a white, wooden bed frame with a floral-patterned coverlet. Two pillows and a decorative cushion rest against the headboard. A bedside table holds a lamp, and natural light enters through a window with soft curtains.
Guest suite in Chincoteague
4.94 out of 5 average rating, 357 reviews

Baywatch North-Waterfront & Roaming Ponies

Lovely space! 2 bedroom/1 bath vacation efficiency, decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

ValueLocationBreakfast

Top guest favourite
A private bedroom features a spacious bed with a detailed headboard, adorned with decorative pillows. Natural light fills the room through large windows, highlighting a cozy area rug and a bedside table with a lamp. A decorative shelf is present, providing additional storage.
Flat in Accomac
4.97 out of 5 average rating, 101 reviews

Modern First Story Apt Open Floor Plan

Relax with the whole family at this peaceful place to stay. There are two units available with separate outside entrances to this beautiful, new constructed home conveniently located just 1/4 mile off of Route 13 and less than an hour from area beaches. The units can be rented together or separately if you need more space for your family gathering. This listing is for Unit 1, the downstairs, which includes a front porch and back porch.

FamilyLocationLaundry

Guest favourite
A modern kitchen is presented with white cabinetry and stainless-steel appliances, featuring a refrigerator, microwave, and coffee maker. A dining table is set for four, and a cozy seating area with a blue couch is visible. Natural light enters through a window, enhancing the space.
Cottage in Chincoteague
4.93 out of 5 average rating, 122 reviews

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!

LocationFamilyPool

Guest favourite
Home in Chincoteague
5.0 out of 5 average rating, 16 reviews

Sunset Dreams

Sunset Serenity: Walk to Pony Parade & Downtown The Space Experience the best of island living in this sun-drenched, two-story townhouse. Tucked away on a peaceful side road, our home offers a quiet escape while keeping you minutes from the heart of the action. Relax in the airy living room and enjoy the glow of the sunset after a long day at the beach—this is your perfect coastal basecamp.

LocationFamilyNearby

Popular amenities for Chincoteague holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Chincoteague's top sights

Chincoteague Island

74 locals recommend

Assateague Beach

35 locals recommend

The Bike Depot

13 locals recommend

Island Theatre

11 locals recommend

Chincoteague Island Outfitters

9 locals recommend

Wallops Island

4 locals recommend

Other great holiday rentals in Chincoteague

Top guest favourite
A hot tub is situated on a wooden deck, bubbles rising gently from the water's surface. The vibrant blue exterior of the house is contrasted by pink trim. Sunlight reflects off the hot tub, creating a bright and inviting ambiance. A screened porch and balcony are visible in the background.
Home in Chincoteague
4.98 out of 5 average rating, 54 reviews

Hot Tub. Fire pit. Fenced Yard. Games. Downtown.

LocationValueKitchen

Top guest favourite
A spacious living area features a large sectional couch and a coffee table, surrounded by wooden flooring. A world map adorns the wall, and natural light streams in through the windows. The open layout flows into a dining area visible in the background.
Home in Chincoteague
5.0 out of 5 average rating, 52 reviews

The Magnolia House ~Available Aug.24th 30th~

LocationFamilyGetting around

Guest favourite
A gravel driveway leads towards a rustic boathouse with weathered wooden siding, framed by tall grasses and marshland. The iconic Chincoteague lighthouse can be seen in the distance, completing the scenic view under a clear sky.
Cabin in Chincoteague
4.91 out of 5 average rating, 82 reviews

The Boathouse: Charming & Historic Waterfront Stay

FamilyLocationParks

Top guest favourite
The inviting exterior of the cottage is framed by lush greenery, featuring a charming front door and welcoming pathway. A bicycle leans against the railing, while vibrant flowers and decorative landscaping enhance the coastal appeal. Natural light brightens the front of the house.
Home in Chincoteague
5.0 out of 5 average rating, 44 reviews

The Cottage Bluefish -newly remodeled for '26

LocationFamilyIndoor spaces

Top guest favourite
The front exterior of a charming house features a peaked roof and a welcoming entrance. Large windows provide ample natural light, framed by a neutral color scheme. A stone pathway leads to the front door, surrounded by a landscaped area with decorative rocks and seasonal plants.
Home in Chincoteague
4.98 out of 5 average rating, 51 reviews

The Shell Hunter

FamilyLocationBack garden

Guest favourite
A spacious living area features a plush leather sectional sofa facing a mounted television. Light floods the space through large windows adorned with sheer curtains. A wooden coffee table sits centrally, and a ceiling fan is positioned above, enhancing the comfortable ambiance.
Flat in Chincoteague
4.83 out of 5 average rating, 23 reviews

Main Street Magic

FamilyLocationCleanliness

Guest favourite
A modern kitchen area features stainless steel appliances, including a stove, microwave, and refrigerator. Light-colored cabinets provide storage, while a small rug adds comfort to the floor. A separate sleeping area is visible in the background, highlighted by warm tones.
Flat in Chincoteague
4.81 out of 5 average rating, 74 reviews

Mini Slice of Island Heaven

ValueFamilyKitchen

Guest favourite
A 38ft Holiday Mansion is anchored at the marina, featuring a spacious top deck with two blue chairs. The exterior showcases a combination of white and teal colors, with large windows for ample natural light. The surrounding water reflects the clear blue sky.
Houseboat in Snow Hill
4.89 out of 5 average rating, 37 reviews

The Tranquil Traveler

FamilyLocationCleanliness

When is the best time to visit Chincoteague?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$189 SGD$183 SGD$191 SGD$192 SGD$223 SGD$308 SGD$351 SGD$319 SGD$235 SGD$200 SGD$189 SGD$191 SGD
Avg. temp3°C4°C8°C13°C18°C23°C26°C25°C22°C16°C10°C6°C

Frequently Asked Questions

  • What are the best places to stay in Chincoteague?

    Many visitors choose accommodations near Main Street for walkable access to shops and dining or stays around Maddox Boulevard for proximity to nature and the beach. Waterfront rentals are often suggested for those who appreciate sunrise views.

  • What are the best things to do in Chincoteague with kids?

    Kids can explore sandy beaches, build sandcastles, or search for seashells around Chincoteague. Visiting the local wildlife refuge, miniature golf, and boat tours to spot ponies and dolphins are often recommended family activities.

  • What are some of the best things to do in Chincoteague?

    Explore sandy shores, kayaking trails, and nearby nature preserves around Chincoteague. Photography, birdwatching, and sampling local seafood are also frequently suggested for a laid-back experience.

  • How is the weather in Chincoteague?

    Chincoteague has mild winters ranging from 29–51°F (-1–10°C) and warm, humid summers between 70–86°F (21–30°C). Rain is spread throughout the year, with summer months typically being wetter.

  • When is the best time to visit Chincoteague?

    Late spring through early fall is often recommended for milder weather, blooming wildflowers, and community events. Pony activities and warmer beach days typically draw visitors during summer months.

  • What are the best places to visit in Chincoteague?

    Chincoteague National Wildlife Refuge, Assateague Lighthouse, and the historic downtown area are often mentioned for their natural beauty and local culture. The Assateague Island beach is another popular spot for relaxation.

  • What are some hiking trails in Chincoteague?

    Explore nature trails around Chincoteague National Wildlife Refuge, where paths wind past marshes, forests, and coastal landscapes. These trails are often suggested for spotting birds and glimpsing the island's wild ponies.

  • What are some family activities we can do in Chincoteague?

    Chincoteague has boat tours, sandy beaches, and nature hikes for all ages. Families frequently enjoy biking around the island, visiting wildlife refuges, and exploring local ice cream shops or maritime museums.

  • What are some of the best day trip ideas from Chincoteague?

    Day trips often include nature preserves, historic lighthouses, and small neighboring towns with seafood markets. Art galleries, kayaking adventures, and nearby bayfront parks are also frequently suggested for a change of scenery.

  • Are there any pet friendly accommodations available in Chincoteague?

    Chincoteague has pet-friendly vacation rentals in neighborhoods near the water and across the island. Many hosts welcome dogs, so be sure to review each listing for specific rules and amenities.

  • What are some local tips for visiting Chincoteague?

    Bring insect repellent for marshy areas, especially in warmer months, and plan for sun protection at the beach. Local markets are great for fresh seafood, and early mornings are quieter for nature viewing.

  • What is Chincoteague known for?

    Chincoteague is known for its wild ponies, sandy beaches, and diverse wildlife. The town has a laid-back atmosphere and draws visitors seeking outdoor recreation, birdwatching, and traditional seafood.

  • What are the best hidden gems to explore in Chincoteague?

    Tucked-away art studios, smaller marsh trails, and quiet waterfront piers are often recommended by locals. Field stations and maritime exhibits also invite visitors to learn more about the island’s natural history.

  • What are the best foods to try in Chincoteague?

    Chincoteague is known for fresh oysters, clams, and locally caught blue crab. Soft-shell crab sandwiches, cream-based seafood soups, and homemade ice cream are also frequently suggested by locals.

  • What should I bring for a trip to Chincoteague?

    Pack sun protection, insect repellent, swimwear, and comfortable shoes for outdoor exploration. A light jacket and rain gear are helpful, as the island has varied weather and coastal breezes.

  • What is the nightlife in Chincoteague like?

    Chincoteague has a relaxed nightlife with casual waterfront restaurants, ice cream parlors, and occasional live music. Locals and visitors often enjoy sunset strolls and conversation at laid-back venues.

  • What are the most popular events or festivals in Chincoteague?

    The Chincoteague Pony Swim during late July is the most well-known event, drawing large crowds to watch the wild ponies. Fall festivals, outdoor art shows, and seafood celebrations are popular throughout the year.

  • Are there family friendly vacation rentals in Chincoteague?

    Family-friendly vacation rentals can be found throughout Chincoteague, including options with outdoor spaces, bunk beds, or easy access to parks and beaches. Some rentals are located near playgrounds and ice cream shops for added convenience.

Destinations to explore