Family-friendly holiday rentals in Eastern Shore of Virginia

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Eastern Shore of Virginia

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

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Guest favourite

Cottage in Heathsville

4.94 out of 5 average rating, 179 reviews

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

We welcome you to stay at "HedgeRow" a deer haven on the Great Wicomico River, located in a hidden corner of the popular Northern Neck of Virginia. You'll be delighted in all the area and this charming listing has to offer. Located just 10 minutes from Kilmarnock, enjoy wineries, shopping and local attractions nearby. Bring your boat, kayaks, fishing rods or friends, then relax in all things that encompass river life. There is a boat ramp and fishing dock available for guests use (Adults Only).

8–15 Sep

$167 SGD per night

Guest favourite

Tiny home in Accomac

4.93 out of 5 average rating, 441 reviews

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a tiny house with big charm. This rural cottage on a 50 acre farm is nestled between peaceful fields, woods, marsh and creek. Curated with hygge comfort and efficiency in mind, you'll love the natural light and serene decor. • Epic stargazing • Heavenly private outdoor shower • Firepit with wood provided • Ample open spaces • Peace and quiet for sleeping • Comfy patio seating for chilling, coffee, and cocktails • Fast Starlink WIFI. • Proud Superhost for 10+ years!

10–17 Feb

$166 SGD per night

Guest favourite

Bungalow in Belle Haven

4.92 out of 5 average rating, 178 reviews

Stay Waterfront-Private Dock Belle Haven Bungalow

Come explore the Eastern Shore - Waterfront bungalow with fishing / crabbing pier. Our two bedroom, two bath bungalow sleeps up to 7 guests comfortably. Open floor plan and large screened porch / deck make our modest bungalow feel like a much bigger place. Perfect setting for a family vacation you will never forget. Kayaks, Fishing / crabbing gear and yard games are all available for use during your stay. 35 minute drive to Cape Charles beach and many other adventures in every direction.

21–28 Sep

$261 SGD per night

Guest favourite

Cottage in Onancock

4.96 out of 5 average rating, 138 reviews

A "True" Chesapeake Bay Waterfront Experience!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

15–22 Nov

$467 SGD per night

Guest favourite

Flat in Lexington Park

4.97 out of 5 average rating, 511 reviews

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

19–26 Feb

$155 SGD per night

Guest favourite

Cottage in California

4.97 out of 5 average rating, 195 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

20–27 Apr

$121 SGD per night

Guest favourite

Guest suite in Dunnsville

5.0 out of 5 average rating, 239 reviews

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

This is a studio apartment above detached garage, with a balcony and seating. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance and bathroom, which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. We have self check in and ample space for social distancing. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

7–14 Jul

$157 SGD per night

Guest favourite

Home in Crisfield

4.95 out of 5 average rating, 254 reviews

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

15–22 Mar

$217 SGD per night

Guest favourite

Cottage in Gloucester Courthouse

4.98 out of 5 average rating, 195 reviews

Historic Ware River Cottage at Glebefield

Come visit this quiet and peaceful setting on the Ware River in historic Gloucester VA. The cottage sits on a 65 acre waterfront property. This fully updated cozy cottage is a great home base for exploring Williamsburg, Yorktown, Jamestown and Richmond. Pets are welcome with a small fee and pre-approval. There are serval buildings and gardens to enjoy so please take note of the picture captions for details on the cottage and other dependencies.

1–8 Jan

$226 SGD per night

Guest favourite

Home in Williamsburg

4.97 out of 5 average rating, 178 reviews

Casita on the Corner

Our cozy little 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens/Water Country. This area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. Take a tour on The Colonial Parkway or If you are a cyclist bring your bike and ride the Capitol trail or hit the trails at Freedom Park or New Quarter Park.

24–31 Jan

$175 SGD per night

Guest favourite

Cottage in Gwynn

4.96 out of 5 average rating, 200 reviews

Mystic Seahorse Cottage & game room

Welcome to our quiet corner of Gwynn’s Island! It may be cool outside but you can relax inside with a movie, hang out in the heated game room, warm up around the firepit, or take a walk to the beach. The cottage is clean and stocked with everything you need for a relaxing visit. Drive 10 minutes to Mathews for great restaurants and shopping, or an hour to Yorktown, Jamestown and Williamsburg. Come relax and enjoy some Island Time with us!

19–26 Oct

$199 SGD per night

Guest favourite

Cabin in Deltaville

4.97 out of 5 average rating, 253 reviews

"The Little Red Cabin" aka The Galley

Called the "The Galley". This is the first cabin built on the property. Right on the water with views of the Bay and beach. Galley kitchen, bedroom, small bathroom with shower, family room with a fireplace and dining area. Big screened in porch w/ fabulous breezes. Literally, right on the water!!! NO PETS.

2–9 Apr

$150 SGD per night