Family-friendly holiday rentals in Chincoteague Bay

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Top-rated family-friendly rentals in Chincoteague Bay

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
A comfortable blue futon is positioned against a large window, offering views of the marina and surrounding greenery. Two pillows, one with a floral design and another with a cheerful message, add a decorative touch. Natural light fills the space, accentuating the wooden walls.
Houseboat in Snow Hill
4.8 out of 5 average rating, 171 reviews

"Serendipity"- Houseboat Getaway

A "Tiny house on the water". Your home-base for exploring Delmarva! Serendipity is a vintage 36ft Holiday Mansion, 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. Serendipity 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!

Top Guest favourite
Four colorful tiny cottage suites are aligned under a blue sky with fluffy clouds. Each suite features distinct pastel-colored exteriors with round windows and front doors in various hues, complemented by modern railings and landscaping that enhances the welcoming vibe.
Tiny home in Lower Township
5 out of 5 average rating, 263 reviews

Hot Tub | Mini Golf | Arcade | Gym — Coastal Quad

Welcome to The Coastal Quad, New Jersey’s first pocket resort! You will be booking a stay in one of four luxurious, 1BR tiny cottage suites, so each visit is a new adventure! You will enjoy your own private hot tub, fire pit, grill, fenced-in yard, and access to a shared rooftop mini golf course, retro arcade, full gym with sauna, office, laundry facility and more. Located just steps from a quiet bay beach and a short drive to Cape May and Wildwood, this is the most exciting resort at the shore!

Top Guest favourite
A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.
Cottage in Hacksneck
4.95 out of 5 average rating, 154 reviews

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Top Guest favourite
Guest suite in Delmar
5 out of 5 average rating, 134 reviews

The Red Maple Studio minutes from Salisbury!

Red Maple Studio is a private 1‑bedroom studio on a quiet street in historic Delmar, MD. Kylan Barn – 6 min. Venue 54 – 7 min. Downtown Salisbury – 15 min. SU – 20 min. OCMD – 45 min. Sleeps 4 with king bed and pull‑out couch. Workspace, fast WiFi, kitchenette (no cooking), private laundry. Safe neighborhood, off‑street parking, well‑lit walkways. Private backyard patio with 6’ fence. Stylish, super clean and comfortable. Sorry….no 3rd‑party bookings, pets, parties, indoor smoking or cooking.

Top Guest favourite
A rustic treehouse is elevated among tall trees, featuring a front porch with a railing and multiple windows. Below, a seating area is arranged with bright blue chairs and a black coffee table, surrounded by a natural forest setting.
Treehouse in Machipongo
4.97 out of 5 average rating, 117 reviews

The Waverly Treehouse

Reconnect with nature and sway with the trees in this rustic treehouse nestled away in the woods with a gorgeous view of Hungar's creek. Enjoy the view from the front porch or while relaxing around the fire pit. Visit the adorable beach town of Cape Charles, complete with a beautiful beach, brewery, distillery and plenty of restaurant options, or stop by the nearby vineyard for some local wine. Usage of dock, kayaks, grill, and fire pit all included. Beach towels and cooler also provided.

Top Guest favourite
Cottage in Leonardtown
4.96 out of 5 average rating, 260 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

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, 521 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 :)

Top Guest favourite
The interior of the tiny cabin showcases a unique staircase leading to a lofted sleeping area. Natural wood elements are highlighted throughout, with a clear roof allowing natural light to fill the space. A doorway opens to the outdoors, enhancing the cabin's connection to nature.
Tiny home in Diggs
4.95 out of 5 average rating, 226 reviews

Stargazer Tiny Cabin

(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

Top Guest favourite
The interior of the bus features a cozy layout with wood paneling and large windows providing natural light. A comfortable seating area, equipped with pillows, is situated next to a compact kitchen with a stove and cabinets. A small dining table with two placemats is visible.
Bus in Frankford
4.96 out of 5 average rating, 168 reviews

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

Top Guest favourite
A modern barn-style exterior is shown with a soft twilight glow. Inside, a cozy loft bedroom features a spacious bed adorned with decorative pillows. A bright dining area is visible, highlighting wooden accents and seating. Two playful goats are seen exploring their cozy enclosure.
Loft in Pocomoke City
4.98 out of 5 average rating, 117 reviews

Cozy Barn Loft: Country Views & Central to Beaches

Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

Top Guest favourite
A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.
Home in Newark
5 out of 5 average rating, 116 reviews

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

Guest favourite
A wooden staircase illuminated by soft lights leads down to a private dock. Reflections of trees and evening sky are seen on the calm water of St. Leonard Creek. A sailboat is moored at the end of the dock, adding to the serene waterside ambiance.
Cabin in Lusby
4.89 out of 5 average rating, 311 reviews

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.

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