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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, 207 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!🐴🦪🌅

Top guest favourite
Home in Chincoteague
4.96 out of 5 average rating, 104 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!

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

Welcome to the Boathouse! You read that right: Boathouse (not House Boat!) This house, which has been part of our family for generations, is the perfect home-base while you visit the special island of Chincoteague! Watch the lighthouse from across the marsh, go for a canoe ride through the channel, catch some crabs off the private pier, or make your way to the famous Assateague Beach - this cozy, quirky house is perfect for those seeking a unique and memorable adventure on Chincoteague Island!

Top guest favourite
A large wooden deck features several adirondack chairs positioned to face expansive views of the marshland and water. A clear blue sky complements the serene landscape, with gentle clouds casting soft shadows over the scene.
Home in Parksley
5 out of 5 average rating, 23 reviews

Serene Waterfront Metompkin Retreat - Entire Home

Discover serenity at the ultimate retreat on Virginia's Eastern Shore at our waterfront oasis. Indulge in sweeping panoramic views of the tranquil waters that stretch as far as the eye can see. Nature enthusiasts will delight in the abundance of birdlife, making it a true birdwatcher's paradise. Whether sipping coffee on the private deck at sunrise or enjoying a glass of wine while watching the sunset paint the sky, every moment here is a picture-perfect postcard. A truly unforgettable getaway.

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.

Mermaid & Mare – A Downtown Retreat with Hot Tub, Firepit & Pet-Friendly! Escape to an island retreat with two spacious bedrooms, each with an en-suite bath. First-floor bedroom – King bed, walk-in shower, deck access with hot tub. Upstairs bedroom – Jacuzzi tub, balcony with bay views. With 4 beds (1 King, 3 Queens), there’s room for family & friends. Amenities: Hot tub, firepit, cornhole & pet-friendly backyard, Smart TVs, screened porch, & bay-view decks. Walk to restaurants, bars & shops.

Guest favourite
A spacious family room showcases a large sectional couch in a neutral tone, complemented by decorative pillows. A TV is mounted on the wall above a modern fireplace, with natural light filtering through the window blinds.
Home in Chincoteague
4.9 out of 5 average rating, 120 reviews

Chincoteague Island Creekside Cottage

Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal small town". Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponys) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124". Make Memories!

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, 202 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!

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 out of 5 average rating, 52 reviews

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

You and your family will love this 100 year old fully restored home with its original hard wood floors, brand new chef’s kitchen, the 75’ TV and the extra large couch. Plan to pack your beach towels, your favorite swim suit and make yourself at home here in our Magnolia House. Located only 2 blocks from Maddox and only 5 miles from the beach. The bike trail to the beach starts right in our backyard. We hope to have created a space you can’t wait to come back to.

Guest favourite
Home in Chincoteague
4.86 out of 5 average rating, 128 reviews

Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

Location, Location, Location! Sunny Claire puts you in the heart of historic downtown Chincoteague, just minutes from Assateague Beach and the National Wildlife Refuge. Steps from top restaurants, shops, and attractions, this charming retreat features a 6-person hot tub, cozy porches with partial water views, and sunset-ready vibes. Enjoy a King Sleep Number bed, linens and towels provided, an outdoor shower, and a water filtration system for a carefree stay.

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, 120 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!

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 out of 5 average rating, 43 reviews

The Cottage Bluefish -newly remodeled for '26

Looking for the quintessential Chincoteague island retreat to make lasting memories? Welcome to COTTAGE BLUEFISH, a Chincoteague Island hideaway lovingly restored and newly available for the 2026 rental season. This island cottage offers classic Chincoteague seaside look & vibe, combined with fresh, clean, newly remodeled everything. Discerning guests will not be disappointed. Fresh bedding and linens are provided.

Guest favourite
Home in Chincoteague
5 out of 5 average rating, 15 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.

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

Guest favourite
Cabin in Chincoteague
5 out of 5 average rating, 7 reviews

Sharkeys | Coastal Cabin-Water View + Sunset

A sleek building is situated by the water's edge, reflecting the soft hues of a sunset. Clouds scatter across the sky, casting gentle shadows, while pilings extend from the shore into the tranquil bay. The serene scene invites relaxation and appreciation of the natural beauty.
Apartment in Chincoteague
4.69 out of 5 average rating, 337 reviews

The Little Paradise-Waterfront, pet-friendly Studio

Superhost
Two wooden Adirondack chairs are positioned on a weathered dock, facing towards a calm waterway. A shaded structure is visible on the left, while boats are anchored in the distance against a backdrop of blue skies dotted with white clouds.
Cottage in Chincoteague
4.73 out of 5 average rating, 113 reviews

SNUG HARBOR waterfront cottage with a grand view!

Top guest favourite
A serene sunset is captured over the water, with the sun gently descending on the horizon. Silhouette of dock pilings is visible against the shimmering surface of the water. Tall grasses in the foreground reflect warm hues of orange and pink, enhancing the tranquil scene.
Home in Chincoteague
4.98 out of 5 average rating, 97 reviews

Waterfront-Views from all rooms-CI bay sunset

Top guest favourite
A two-story waterfront home is visible, elevated on stilts with a spacious deck featuring steps leading down to a private dock. Brightly colored kayaks are stored on the dock, and lush trees surround the property, providing a natural, serene backdrop.
Home in Chincoteague
4.97 out of 5 average rating, 94 reviews

Jay's Retreat: dock, kayaks, EV charger, bikes

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, 63 reviews

Waterfowl Watch Chincoteague & bikes Fall dates

Guest favourite
A charming single-story home is presented, featuring a covered front porch with white railings, situated on a grassy lawn. The building is complemented by dark shutters and a light exterior, with a gravel driveway leading to the barn area visible in the background.
Home in Chincoteague
4.97 out of 5 average rating, 36 reviews

‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!

Top guest favourite
A charming two-story island home is nestled among tall trees, providing a natural setting. The structure features a sloped roof and a front porch with a railing. Sunlight filters through the branches, casting dappled shadows on the ground.
Home in Chincoteague
4.97 out of 5 average rating, 199 reviews

Charming Island Home "Sandy Pines"

When is the best time to visit Chincoteague?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$191 SGD$184 SGD$192 SGD$193 SGD$224 SGD$310 SGD$353 SGD$321 SGD$237 SGD$201 SGD$191 SGD$192 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