
Family-friendly vacation rentals in Cape Charles
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Cape Charles
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

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.

Family Holiday Home- Outdoor Fireplace &Huge Patio
You'll experience the magic of Cape Charles Historic District in a home where modern convenience meets classic charm! Sunshine Rays is your premier family vacation rental, consistently rated 5 stars by guests who praise its cleanliness, thoughtful stocking, and incredible amenities. Perfect for up to eight guests, you are situated on a quiet, friendly street. You'll enjoy a peaceful walk to the Cape Charles beach and close to Central Park and the bustling shops and restaurants of Mason Avenue.

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!

Stylishly Renovated | Golf Cart Avail. | Bakery!
Nectarine 15 is centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

Bay Breeze on Tazewell (Sun-Sun rental June-Aug.)
Bay Breeze on Tazewell is a recently remodeled Cassatt cottage with historic charm and modern amenities. The home includes a fabulous, sunny kitchen stocked to meet your needs. We provide fresh linens and towels for your stay. In the shed, you will find lots of items for the beach, a wagon, and bikes which we are happy to share. Bay Breeze is just a short walk to the beach, various restaurants, boutiques, and marina. If our home is not available, try our new Airbnb home ...Harbor View!

3 Blocks to Beach, Fenced Backyard, Pet Friendly!
Welcome to Peach Haven, a newly renovated duplex in the Cape Charles historic district. Just 1 block from the park and 3 blocks from the beach, it's the ideal base for your Cape Charles escape. This pet-friendly rental sleeps five guests comfortably with a master bedroom (queen bed) and a second bedroom with a custom-made full-over-full bunkbed. The house has been thoughtfully stocked with everything you'll need for a comfortable stay. Need more space? Ask about renting the other side, too!

Summer Camp Tiny Cottage Walk to the beach & shops
At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below! *We have a security camera on the front exterior of the home.

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.

Airstream Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning Airstream retreat 10 mins from Cape Charles. The 1969 Airstream has been converted into a contemporary studio with all the comforts of a luxury hotel room. Wake up to the birds singing in the trees that completely surround the huge front deck. Take a walk on our trails. Enjoy watching the animals. Take a trip into Cape Charles for restaurants and shopping, then enjoy a movie in the Airstream at night.

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.

Steps to the Sea at Salt Box
Escape to The Salt Box, a charming 1915 duplex just one block from the beach in the heart of Cape Charles' Historic District. This cozy, private retreat sits on a peaceful, tree-lined street and is a short stroll to the beach, pier, shops, restaurants, and more! Check out our local Guidebooks or text us anytime—we're happy to share our favorite local spots! Looking for even more space? You can also book the other half of our duplex, Salt Box II!
Popular amenities for Cape Charles family-friendly rentals
Family-friendly home rentals with a hot tub

902C Coastal King Retreat Steps from Beach + Sauna

The Hideaway at Mill Creek

Coastal Red Barn Retreat

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Hot Tub + Walk to Beach! Fully Updated + Spacious

Bay cottage 🏖on the beach. Stunning views🏝

Blue Heron WaterSide

Magical wooded cottage pool +priv hottub walk2town
Family- and pet-friendly home rentals

Waterfront FamilyFriendly Home Improved for 2023

Nan's Place aka Down Easter

A "True" Chesapeake Bay Waterfront Experience!

Relax in Urbanna, @ The Blue Tango!

Centrally Located Sleek Studio Apartment

Bay Breeze Home on private waterfront

"Live Life Sunnyside Up" - Minutes From The Beach!

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

Positano Villa

York River Vacation Home

Gorgeous Vacation House

The Rosé Retreat: Fireplace-Screened Porch-RELAX

“Old Smokey”A cozy, single bedroom, unique getaway

"Shangri-La", of Hampton, Virginia

Pelican Place, Cozy Retreat | Pool | Walk to Tides

The Barn at Pond Point - Riverfront Home
When is the best time to visit Cape Charles?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$49,620 GYD | G$41,873 GYD | G$43,967 GYD | G$47,108 GYD | G$59,879 GYD | G$72,860 GYD | G$77,047 GYD | G$74,116 GYD | G$58,832 GYD | G$54,645 GYD | G$54,645 GYD | G$49,201 GYD |
| Avg. temp | 4°C | 5°C | 8°C | 13°C | 18°C | 23°C | 26°C | 25°C | 22°C | 16°C | 11°C | 6°C |
Quick stats about vacation rentals that are family-friendly in Cape Charles

Total vacation rentals
Explore 250 vacation rentals in Cape Charles

Nightly prices starting at
Cape Charles vacation rentals start at G$20,937 GYD per night before taxes and fees

Verified guest reviews
Over 7,070 verified reviews to help you choose

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
250 of Cape Charles vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cape Charles rentals

4.9 Average rating
Cape Charles stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Northampton County
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
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- First Landing State Park
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