10 Charming Waterfront Getaways in Virginia for a Relaxing Escape
Tired of crowded beaches and tourist traps? Virginia’s hidden coastal gems offer serene waterfront views, small-town charm, and plenty of family-friendly fun. Whether you’re craving wild pony sightings, historic streets, or the best homemade ice cream, these quaint towns deliver the perfect escape. You need to visit these waterfront getaways in Virginia and truly relax.
Why Choose Virginia’s Small-Town Waterfronts?
Skip the hustle of Virginia Beach and discover quieter shores where kids can splash freely, antique shops line walkable streets, and locals greet you with a smile. These towns offer affordable stays, pet-friendly options (hello, Kamo!), and a laid-back vibe that’s perfect for recharging.
Prefer quiet piers over crowded boardwalks? These towns offer affordable charm—plus, many are pet-friendly for stress-free trips with your service dog. For upcoming local events, bookmark Virginia’s Eastern Shore Tourism to plan your visit!
Chincoteague – Where Wild Ponies Roam
Made famous by Misty of Chincoteague, this island paradise is all about wild ponies, sandy shores, and small-town magic. Visit in July for the Chincoteague Pony Swim, a thrilling spectacle where ponies cross the channel from Assateague Island. Kids will love the Chincoteague National Wildlife Refuge, perfect for biking and birdwatching. Stay at the Waterside Inn, a cozy, pet-friendly spot, and grab fresh seafood at Bill’s Prime Seafood & Steaks. Don’t leave without a scoop (or two) from Island Creamery—their homemade waffle cones are legendary!
Must-Do Event: Chincoteague Pony Swim (July)
Onancock – A Hidden Artsy Oasis
Made famous by Misty of Chincoteague, this island paradise is all about wild ponies, sandy shores, and small-town magic. Visit in July for the Chincoteague Pony Swim, a thrilling spectacle where ponies cross the channel from Assateague Island. Kids will love the Chincoteague National Wildlife Refuge, perfect for biking and birdwatching. Stay at the Waterside Inn, a cozy, pet-friendly spot, and grab fresh seafood at Bill’s Prime Seafood & Steaks. Don’t leave without a scoop (or two) from Island Creamery—their homemade waffle cones are legendary!
Must-Do Event: Chincoteague Pony Swim (July)
Cape Charles – Retro Beach Bliss
With its sandy shores and throwback charm, Cape Charles is Virginia’s best-kept beach secret. Stay at the Bay Haven Inn, a cozy B&B, and grab a bite at The Shanty, known for its waterfront dining. Kids will adore the Cape Charles Beach—calm, shallow waters make it perfect for little ones. For dessert, Brown Dog Ice Cream serves up creative flavors like lavender honey. Don’t miss the Cape Charles Summer Concert Series under the stars!
Must-Do Event: Summer Concert Series (June-August)
Irvington – Coastal Elegance Meets Small-Town Vibes
Fancy a little luxury? Irvington delivers with upscale boutiques and waterfront mansions. Stay at The Tides Inn, where you can kayak right from the resort. Dine at Trick Dog Café for gourmet sandwiches, then browse the Irvington Farmers Market (Saturdays, May-Oct). Kids will love the Steamboat Era Museum, showcasing Virginia’s riverboat history.
Must-Do Event: Irvington Farmers Market (Saturdays, May-Oct)
Montross – History & Riverfront Adventures
A hidden gem on the Potomac, Montross is packed with history and outdoor fun. Stay at the George Washington Birthplace B&B, then explore Westmoreland State Park, where kids can hunt for fossilized shark teeth. Grab a slice at Angelo’s Pizza, a local favorite. Don’t miss the Montross Fall Festival in October, featuring crafts, music, and food trucks.
Must-Do Event: Montross Fall Festival (October)
Kilmarnock – Festivals & Small-Town Fun
This lively town throws some of Virginia’s best festivals! Visit in December for the Christmas Light Boat Parade, where boats decked in lights glide through the harbor. Stay at the Kilmarnock Inn, a historic charmer, and eat at The Local for farm-to-table goodness. Kids will love Good Luck Cellars, where parents can sip wine while little ones picnic outside.
Must-Do Event: Christmas Light Boat Parade (December)
Urbanna – The Oyster Capital of Virginia
Oyster lovers, rejoice! Urbanna hosts the Urbanna Oyster Festival every November, a must-visit for seafood fans. Stay at the Urbanna Inn, a historic retreat, and eat at Something Different for Southern comfort food. Kids will love watching boats at the Urbanna Creek Marina.
Must-Do Event: Urbanna Oyster Festival (November)
Reedville – A Step Back in Time
This fishing village feels like a living museum. Stay at Gables & Grace B&B, dine at Crazy Crab, and explore the Fishermen’s Museum. Visit in May for the Reedville Bluefish Derby, a fun fishing tournament.
Must-Do Event: Reedville Bluefish Derby (May)
Deltaville – Sailing & Sandy Toes
A sailor’s paradise, Deltaville offers quiet beaches and maritime charm. Stay at Deltaville Marina & Resort, eat at Cocomo’s, and rent a boat for a family adventure.
Smithfield – Ham, History & Waterfront Walks
Famous for its salty ham, Smithfield is a foodie’s dream. Stay at Smithfield Station, indulge at Smithfield Ice Cream Parlor, and explore Windsor Castle Park.
Good to Know Before You Go
✔ Best Time to Visit: Spring-Fall for festivals and warm weather.
✔ Pet-Friendly? Many spots welcome service animals—always call ahead!
✔ Budget Tip: Rent a cottage for longer stays to save.
Psst—traveling with Kamo? Our Service Animal Travel Guide covers everything from lodging to local leash laws. And for seasonal fun, Eastern Shore events highlight can’t-miss festivals like the Chincoteague Pony Swim!
Don’t Miss These BucketList Coastal Celebrations!
Plan your perfect small-town getaway with this guide to Virginia’s best waterfront festivals, parades, and family-friendly fun.
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