
Places to stay near Chincoteague Island
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Top-rated holiday rentals near Chincoteague Island
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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!🐴🦪🌅

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!

Bell Farm Cottage Quiet, Tranquil and Peaceful
Cozy cottage located on a quiet backroad overlooking a wide open field with a deck that provides warm & sunny space for relaxing or reading a book. BFC has a warm farm house feel w/ a touch of the beach. Our kitchen is fully equipped w/ all you need to cook. BFC is located only a few miles from both seaside and bayside boat ramps. A 5 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wachapreague, Wallops & Chincoteague are just a short drive away.

Mins to Beach~Walk to Food and Drinks +Beach Gear!
You'll Experience the ultimate in coastal living at your beautifully renovated vacation home, a stone's throw from the Beach road. This is your perfect getaway destination. You'll enjoy a bright chef's kitchen with granite countertops and a tiled backsplash, open-concept first floor with cozy living room, and a convenient half bath. Retire to the second level where 2 bedrooms await, including a primary suite with a private bath & private balcony for sipping your coffee & serene morning views 🌄

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.

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.

Rest A'Shored charming Chincoteague getaway
Spacious open floor plan great for entertaining family and friends with all the modern amenities you need! Eat inside at the large dining room table or enjoy the cool evening breeze outside on the fully screened in porch. 3 bedrooms and 2 full baths can comfortably accommodate 2 families with children or 3 couples. Located on Willow street, you are just a short walk to the Chincoteague carnival grounds and Main Street. We are dog friendly as we know they are really part of the family!

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 :)

"Beebe Lynn" - Houseboat Getaway
A "Tiny house on the water". Your home-base for exploring Delmarva! Beebe Lynn is a vintage 32 ft Carver, nestled at Baywater Landing Marina in the stunning salt-water marshes of the Chincoteague Bay. From here, you are 35 minutes from Ocean City, MD, and 45 minutes from Chincoteague Island, VA. Beebe Lynn remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

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!

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!

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.
Popular amenities for holiday rentals near Chincoteague Island
Other top sights near Chincoteague Island
Condo rentals with Wi-Fi

Caramar Couples Retreat

Ocean Side 1BR / 1.5BA Renovated Modern Condo

Gorgeous Beachfront! King Bed, Direct Ocean View!

Oceanfront Paradise | Pool | Hot Tub | Beach

Oceanside Charm, desirable midtown Ocean City, MD

Coastal and Bright Oceanfront Condo

Lovely 1 bedroom condo/only 2 blocks to the beach

One Bedroom Beachfront Apartment Mid-Town
Family-friendly house rentals

Heartsong Farmhouse , a nature lover's retreat.

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Dragonfli Bay House on Chincoteague Island

Seas the Day Getaway ~ Pool ~ ONLY 3 mi to BEACH

Bayfront Modern Retreat • Dock, Kayaks, Views

On a Whim, a family retreat!

Coastal Daze-next to Pickleball Court & Playground

Sunset Dreams
Apartment rentals with air conditioning

Modern 2nd-Story Studio Apartment

Pansy’s Retreat

Bright and Airy Oceanside Condo

Cozy Modern Escape w/ Private Patio

Oceanside Condo Steps From Beach

Lovely 2 bedroom overlooking Main St.

Handful of Beach Heaven!

Central AC, Luxury Bathrooms, 4 blocks to Beach!
Other great holiday rentals near Chincoteague Island

Cozy Barn Loft: Country Views & Central to Beaches

Baywatch North-Waterfront & Roaming Ponies

Rumbley Cottage on the Tangier Sound-Private Beach

Holiday Cottages -"Sea Star"~POOL~3 mi. to Beach

New house, Bay views, 4 Beds, Game room

The Starfish House - Key Westy vibe - ‘26 fresh

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

The Boathouse: Charming & Historic Waterfront Stay
Frequently Asked Questions
Where is Chincoteague Island located?
Chincoteague Island is found along the eastern coast of Virginia, bordered by marshlands, waterways, and close to Assateague Island. It is known for its scenic landscapes, distinctive wildlife, and relaxed coastal setting.
When is the best time to visit Chincoteague Island?
Late spring and summer are frequently suggested for warmer temperatures and beach activities, while autumn brings quieter surroundings and mild weather. Wildlife viewing, especially for the famous ponies, often draws visitors during these months.
What are some things to do near Chincoteague Island?
Chincoteague Island has wildlife tours, nature trails, kayaking, and local dining along the waterfront. Around the area, visitors often explore Chincoteague National Wildlife Refuge, see wild ponies, or enjoy sandy beaches.
How is the weather near Chincoteague Island?
Chincoteague Island has cool winters around 29–46°F (-1–8°C) and warm summers reaching 70–86°F (21–30°C). Rainfall is steady year-round with the highest amounts in late summer and fall; a light jacket and umbrella are often suggested.
Destinations to explore
- Chesapeake Bay
- Assateague Island National Seashore
- Ocean City Beach
- Ocean City Boardwalk
- Assateague State Park
- Bethany Beach Boardwalk
- Northside Park
- Ocean City Boardwalk
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Roland E Powell Convention Center
- Ocean Pines Golf Club
- Bear Trap Dunes
- Old Pro Golf
- Salisbury Zoo
- Trimper Rides of Ocean City
- Holts Landing State Park
- NASA’s Wallops Flight Facility Visitor Center
- Splash Mountain Water Park
- Jolly Roger at the Pier
- Layton's Chance Vineyard and Winery





