
Family-friendly vacation rentals in Eastern Shore of Virginia
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Top-rated family-friendly rentals in Eastern Shore of Virginia
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Little Red House on a Farm - Quiet Rural Waterview
The Little Red House VA is a cozy tiny home on a 50-acre farm, surrounded by fields, woods, marsh, and a creek. Curated with hygge comfort and efficiency, you'll love the natural light and calm decor. • Escape the noise & reset in nature • Peaceful sleeping • Thoughtful interior design • Large full bath • Comfy patio for coffee, cocktails, and epic stargazing • Firepit with wood provided • Large private outdoor shower surrounded by woods • Wide open spaces • Fast WIFI • Superhost for 10+ years

Moody Modern Cottage Hot Tub-Fire Pit-Creek views
Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

Guesthouse at Vessel Farm & Winery, Waterfront
Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Eastern Shore Romantic Waterfront Getaway Upscale
A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

Bell Farm Cottage LLC - quiet and peaceful
Cozy cottage located on a quiet backroad overlooking a wide open field & back deck provides warm & sunny space for relaxing or reading a book. The kitchen is fully equipped. BFC has a warm farm house feel w/ a touch of the beach. The bathroom has been updated to a more modern feel. Located only a few miles from both seaside and bayside boat ramps. A 7 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wallops & Chincoteague are just a short drive.

The Cheriton Loft
Located in the heart of Cheriton, The Loft is a bright and sunny apartment. It is perfect for a couple and one child, three friends or one person. Cheriton is an up and coming village which is home to several galleries and an art center. It is less than 4 miles to the charming town and beach of Cape Charles, 3 miles to Oyster Boat Landing and 8 miles to Kiptopeke State Park. The apartment is owned and decorated by"The Sheep Lady", a local painter, illustrator and writer of children's books.

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!

Private romantic pet friendly waterfront cottage
On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Heartsong Farmhouse , a nature lover's retreat.
Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

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.

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 farms’ fire pit in the evening.

The Llama House
Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.
Popular amenities for Eastern Shore of Virginia family-friendly rentals
Family-friendly home rentals with a hot tub

Wooded Wonderland Miniature Golf Hot tub Pool

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

The Hideaway at Mill Creek

Bay cottage 🏖on the beach. Stunning views🏝

Blue Heron WaterSide

Treehouse in the woods w/AC & heat (bath at house)

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Camp Chesapeake House - 6 Acre Waterfront Retreat
Family- and pet-friendly home rentals

The Crab Shack

Waterfront FamilyFriendly Home Improved for 2023

The Bird's Nest at Holly Bluff-Riverfront. Beach.

Tranquil Shores - Nature Inspired Relaxation!

Cozy Beach Cottage

Bay Breeze Home on private waterfront

TooFine Lakehouse, pet friendly waterfront cottage

Historic Ware River Cottage at Glebefield
Family-friendly home rentals with a pool

Country Living Guest House (Upstairs/Downstairs)

Creekside Guesthouse - Dock and Pool on 10 acres

The Rosé Retreat: Kayaks-Screened Porch-RELAX

Ocean Pines Retreat

3 BR Cottage on Mallardee Farm in Williamsburg

Pelican Place, Cozy Retreat | Pool | Walk to Tides

The Barn at Pond Point - Riverfront Home

Historic Rousby Hall, Waterfront, Pool, Beach
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Outer Banks Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- South Jersey Vacation rentals
- Bed and breakfasts Eastern Shore of Virginia
- Villa rentals Eastern Shore of Virginia
- Cottage rentals Eastern Shore of Virginia
- Rentals with a patio Eastern Shore of Virginia
- Cabin rentals Eastern Shore of Virginia
- Rentals with a fire pit Eastern Shore of Virginia
- Rentals with an accessible height bed Eastern Shore of Virginia
- Rentals with outdoor seating Eastern Shore of Virginia
- Apartment rentals Eastern Shore of Virginia
- Fitness-friendly rentals Eastern Shore of Virginia
- Townhouse rentals Eastern Shore of Virginia
- Waterfront rentals Eastern Shore of Virginia
- Rentals with an accessible height toilet Eastern Shore of Virginia
- Pet-friendly rentals Eastern Shore of Virginia
- Rentals with a kayak Eastern Shore of Virginia
- Hotel rentals Eastern Shore of Virginia
- Rentals with a home theater Eastern Shore of Virginia
- House rentals Eastern Shore of Virginia
- Rentals with an EV charger Eastern Shore of Virginia
- Beachfront rentals Eastern Shore of Virginia
- Rentals with lake access Eastern Shore of Virginia
- Rentals with pools Eastern Shore of Virginia
- Rentals with breakfast Eastern Shore of Virginia
- Rentals with a hot tub Eastern Shore of Virginia
- Rentals with beach access Eastern Shore of Virginia
- Rentals with a fireplace Eastern Shore of Virginia
- Condo rentals Eastern Shore of Virginia
- Rentals with a washer and dryer Eastern Shore of Virginia
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Assateague Island National Seashore
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Assateague Beach
- Buckroe Beach and Park
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Wilkins Beach
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park
- Salt Ponds Public Beach
- Parramore Beach
- Guard Shore
- Gloucester Point Beach Par