
Family-friendly holiday rentals in Chincoteague Bay
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Top-rated family-friendly rentals in Chincoteague Bay
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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.

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!

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.

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.

The Laughing King Retreat Honeymoon Island Cottage
Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Farmhouse located on a horse farm
Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Ultimate Cabin Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farmsâ fire pit in the evening.

Hobbs & Rose | A Peaceful Cottage Escape
Built in 1941 from historic âclinker bricks,â this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charmâgorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relaxâweâve created every detail to help you feel restored.

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.

"Jolly"- Houseboat Getaway
#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit
Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Secluded Waterfront 15mi to Beachâ˘Kayaksâ˘Fast WiFi
Casa Blue Heron is a 2,254 ft² (209 m²) custom home offering stunning water views, a firepit, and serene seclusion at our 3-bedroom waterfront sanctuary by Chincoteague Bay and near Assateague, Berlin, Ocean City, Snow Hill and much more. â "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 theâ¤ď¸in the upper-right corner.
Popular amenities for Chincoteague Bay family-friendly rentals
Family-friendly home rentals with a hot tub

Peace Point - Waterfront, Secluded, Home w/hot tub

The Hideaway at Mill Creek

Hot Tub Backyard Oasis! Private Beach, Local Pool

Private point on the Bayđ¤hammock, hot tub, kayaksâ¤ď¸

Waterfront 4-BR home w/ hot tub & charging station

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Beach Please! River cottage w/private beach & dock

Cozy & Content River Retreat Beach Hot Tub & Games
Family- and pet-friendly home rentals

Central Haven with Great Fenced Yard

Waterfront FamilyFriendly Home Improved for 2023

Highbanks House

Relaxing Water Views - Mill Creek Cottage

Forest Grove Retreat

Hideaway on the Bay: Waterfront Vintage A Frame

Little Red House on a Farm - Quiet Rural Waterview

Summer's Seaside Cottage | Near Ponies & Beach
Family-friendly home rentals with a pool

Waterfront, Kayaks, Gameroom, Potomac-2hr from DC

Summer Escape - Dock, Pool, Firepits, & Kayaks

Nature's retreat @ the Bug-a-Boo. Beaches nearby

Kits Cottage on "Just Ducky Acres"

The RosĂŠ Retreat: Pool-Screened Porch-RELAX

Annapolis Garden Suite

The Cozy Cottage At Grateful Meadows

Mosaic Life Escapes -Bayfront Million Dollar Views
Destinations to explore
- Fitness-friendly rentals Chincoteague Bay
- House rentals Chincoteague Bay
- Rentals with a kayak Chincoteague Bay
- Pet-friendly rentals Chincoteague Bay
- Waterfront rentals Chincoteague Bay
- Rentals with a fire pit Chincoteague Bay
- Rentals with outdoor seating Chincoteague Bay
- Rentals with beach access Chincoteague Bay
- Rentals with a washing machine and dryer Chincoteague Bay
- Rentals with a fireplace Chincoteague Bay
- Rentals with pools Chincoteague Bay
- Rentals with a patio Chincoteague Bay
- Family-friendly rentals United States





