Where to Stay on the Eastern Shore

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You’ve heard me share my love for Virginia’s Eastern Shore, but unless you’re from the area that might be a mystery.  What exactly does “Eastern Shore” even mean?

The Eastern Shore peninsula juts out between Chesapeake Bay and the Atlantic Ocean, carefully nestled from it’s Maryland border and connected to the Norfolk/Virginia Beach area via the Chesapeake Bay Bridge Tunnel.

But for an area with a relatively low population — and totally off the tourist radar, except for anyone in spitting distance — there’s a lot packed into this peninsula.  Picking the right base will contribute to your overall experience.  Each town has a different vibe and you can visit them all, but where should you stay on the Eastern Shore?

virginia eastern shore map
Map by Eastern Shore of Virginia Tourism

Where to Stay on the Eastern Shore for Foodies: Cape Charles

The reality of any area with small towns is that food can be hit-or-miss.  Not in Cape Charles.  This small town that I love has great restaurants, ranging from local seafood (oh, those oysters!) to amazingly fresh salads and sides made from local produce.

Bistro Dinner at Hook U Up Gourmet cape charles va
Bistro Dinner at Hook U Up Gourmet

Try breakfasts at Cape Charles Coffee House or sweet potato pancakes at Rayfield’s Pharmacy.  Vote on your favorite type of oyster at The Oyster Farm or plan on three delicious courses at Hook-U-Up Gourmet.  Or keep things simple with sunset views at The Shanty, juicy burgers at Kelly’s Gingernut Pub, or innovative flavors at DeadRise Pies.

Beyond the food, I love that Cape Charles had a warm, shallow bay for swimming, tons of local events, and locals that go out of their way to welcome you.  Try hands-on woodcrafting at the Windsor House, hiking to Savage Neck or Kiptopeke State Park, or even touring an oyster farm.  The Hotel Cape Charles is a boutique property walking distance to everywhere — which is precisely what you want in this small town.

sunset sail in cape charles va
Sunset sail in Cape Charles VA with Cape Charles Boat Tour Company

Brown Dog Ice Cream in Cape Charles (Eastern Shore of Virginia)

By the way, whether you stay in Cape Charles or not, stop in for a cone at Brown Dog Ice Cream.  They’ve won national awards…and the sightDOING seal of approval.

Where to Stay on the Eastern Shore for a Retreat: Machipongo

Small towns, nature, and a beautiful setting lends itself well to a retreat and a chance to disconnect.  If you need to put down your cell phone, stop answering work emails, and clear your head a little bit, I have the perfect place for you.

Machipongo, VA isn’t on anyone’s radar.  There’s nothing there, except an awesome winery you can kayak to (or drive, I suppose).  There are farms, woods, and a few scattered houses that are mostly out of cell phone range.

Plus the Green Valley Bed & Breakfast.

There’s no Wi-Fi, but there are walking trails, a dog that will love you, and an owner that will point you toward some (but not all) of the Eastern Shore’s secrets.  This is the type of place where you stay a week, make a few day trips, but also spend some time by the firepit reading a book or chatting with other guests over coffee in the morning.

If you want privacy on your retreat, this isn’t for you.  But if you want just enough human connection as you share stories about your day with other guests and/or the hostess plus a central location between the lower and middle shore, this is a great pick.

Where to Stay on the Eastern Shore for a Romantic Getaway: Onancock

I liked Onancock, but I was the wrong demographic for my visit.  I was traveling solo, in a town where all you want to do is stroll the streets hand-in-hand with your partner.  You want to watch the sunset at Mallard’s at the Wharf, share a bottle of wine in your room, and hop from art gallery to boutique shop to decorate a home together.

Onancock, Virginia

My goodness, it’s lovely, but the difference between my solo overnight in April and a romantic afternoon with my husband in November was like night and day.

So here’s how to spend your romantic weekend: stop in the Saturday morning farmer’s market (you’ll want to buy everything) and pick up a few things for a picnic.  Try soapmaking or painting at Red Queen Gallery.  Chat with Danny Doughty and save your money for a fabulous piece of folk art.  Alas, being a freelancer doesn’t afford me that luxury yet.

danny doughty gallery onancock
One of these days, I’ll have a powerful painting like these in my house. Mark my words.

Then, snuggle up at The Inn at Onancock.  My stay was wonderful and this traditional bed and breakfast is far more formal than the Green Valley Farm farther south.  Expect decadent breakfasts and lovely outdoor sitting areas.

The romance will come without trying, as soon as you see a canopy bed, gas fireplace, spa-style bathroom, and signature spa robes.  And the best part is…you can enjoy the Eastern Shore from this central location and then take it easy in-between all your fun.

The inn changed ownership since I stayed there, but based on the email newsletters I’ve gotten, the new owners seem just as warm and welcoming as the last ones (and the location and amenities still can’t be beat).  If you go, please tell me if the breakfasts are still decadent!

Where to Go on the Eastern Shore for the Outdoors: Wachapreague

You know how I said picking the right base for your trip will impact your experience?  Well, Wachapreague wasn’t my favorite spot (nor did I spend the night), but I can see the appeal for other travelers so I’m including it here.

Wachapreague, on the ocean side of the peninsula, is built for fishermen.  The area is paradise for in-shore flounder, plus off-shore yellowfin, bluefin, marlin, and more.  You could spend every single day on the water and have an adventure every time.

I stuck to a day trip, on an ecotour to the Barrier Islands with Daytrippers.  We went shelling, birding, and enjoying the scenery — something that everyone on the Eastern Shore loves to do.

barrier islands of eastern shore of virginia
Barrier Islands

When you’re out on the water, it seems as if you’re in the middle of nowhere.  You’ll pass another boat every once in awhile, but you’ll think you have the whole ocean to yourself.  That’s a pretty cool feeling, and a good reason to spend a day on the water, but I’m not sure I’d like to stay overnight.

If you do stay, my vote would be looking for rental units (condos, houses, or otherwise).  After all, you’ll want a kitchen to prepare your daily catch.

Where to Go on the Eastern Shore for Summer Vacation: Chincoteague

Take one look at this sunset and you’ll want to go to Chincoteague.

Sunset in Chincoteague Virginia after a stormy evening.
Sunset in Chincoteague after a stormy evening.

But mostly, I like Chincoteague because it feels like summer vacation to me.  You can rent beach cruisers to cycle around town, stop for ice cream at rivalry locations, and splash in the waves at Assateague Beach.

And then, when you want a twist to your summer vacation activities, you can search for wild ponies, go crabbing, or even watch a rocket launch at NASA’s Wallops Island.

If you only have one day in Chincoteague, I’ve got a great set of plans for you.  If you’d rather be on island time and stay while, it can make a great base as well.  (Don’t tell the state of Virginia, but Chincoteague is also a good place to stay if you want to day trip to Assateague Island State Park in Maryland for more hiking or to Ocean City, Maryland to let the kid in you play for a few hours).

Virginia’s Eastern Shore Has Something for Everyone

I can’t get enough of the Eastern Shore because there are secrets around every corner, but I can understand how overwhelming it can be to choose from a half dozen towns when booking your hotel.

If after this, you’re still confused, it’s okay: choose one, make a few day trips, and next time you’ll know exactly where you want to stay.  Because let’s not kid ourselves…you’ll be planning a return visit before your first trip is over.

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I’ve been to the Eastern Shore three times now, with a fourth trip on my calendar already.  Many thanks to Eastern Shore of Virginia tourism for hosting me.  Obviously it was a good investment on their part since I keep returning!

where to stay on the eastern shore of virginia hotel recommendations

33 thoughts on “Where to Stay on the Eastern Shore”

    1. I’m not connected to this Inn, but I did want to mention that their brunches are award winning. Coastal Virginia Magazine Readers voted their Brunch the Best of the Best in all of the Chesapeake Bay area.

  1. Thanks for the great info on all the little towns have to offer, second time in Cape Charles and love that whole area, love it so much I would love to relocate somewhere in that area, but looking for and apartment, at least 3bedroom, if you know of any, please let me know, my other worries is how many time do they have to evacuate being its a evac. route

    1. Hi Janet! I’ve lived in the eastern shore my whole life and in all that time me and all of my family have lived here we never have had to evacuate. Because of the Chesapeake Bay when hurricanes hit it bounces off the shore and all we ever get is heavy rain and low degree wind. The only place that ever has flooding is back roads. Also there are great apartments in Cape Charles and Onancock but if I were you the small houses in both towns will be a lot better investment for you and your bank account!!

  2. Our family stayed in Wachapreage at a cute 2 bedroom apartment rental above Current Reflections Art Gallery. Very clean and people were very friendly. We got a great breakfast sandwich at the small rustic place across the street before we started our day. Dinner at the Island House. We tried the flounder dinner since Wachapreague is the “flounder capital of the world” according to their signs as you enter the town…Outstanding!

  3. I love the ne’er heard of areas for vacation because I feel like I can just sit back and enjoy the sites, and according to these images, there’s plenty to see.

    I would love to put this on the must-see list!

  4. Thanks for your wonderful summary. The Current Refections fine arts gallery in Wachapreague is a great find. The 2 BR artist apartment above the gallery is a nice place to stay with bookings through the Wachapreague Inn or airbnb. Check out the occasion plein air artist workshops at Current Reflections.

  5. Kiptopeke State Park for cabins or camping if you truly want peace and quiet. Nestled right on the bay, you can have a ranger teach you how to go blue crabbing. They sell what you need right there. You’ll just have to pick up chicken legs as you pass the grocery on the way back from a day trip to Chincoteague Island. I found it nice to be able to eatch sunsets on the Chesapeake Bay from the Kiptopeke State Park beaches. Chincoteague faces East,not west. The Kiptopeke beaches are also amazing for stargazing. Almost the entire southern half of the Eastern Shore is just shy of being an official dark sky stargazing area.

  6. Fun to read about your adventures on the Shore. I recommend a visit to the Barrier Island Center. Wonderful museum and cultural center for the shore life and a beautiful historic location and buildings!

  7. Great summary! I encourage you to come back to Wachapreague. There is so much more than just fishing and hunting. Check out the award-winning Island House Restaurant. Current Reflections Fine Arts Gallery is open on the weekends April – December and always by appointment. The gallery features local and regional artists from Norfolk to Washington, DC. There are also boat tours of the barrier islands – birdwatching and shuttles to private beaches on Dawson Shoals and Cedar Island. William & Mary’s Virginia Institute of Marine Science (VIMS) is also located in Wachapreague. And the Wachapreague Inn is a quaint and friendly place to stay. Also check out the Artist Apartment on airbnb. Thank you!

  8. Cape Charles may have good food, but it is not the foodie capital of the Eastern Shore. That title has long been conceded to the Town of Onancock. *Every* restaurant in town is an award winner. plus they have a great variety of restaurants. From Middle Eastern to traditional crab cakes to a family friendly Irish pub.

    Plus there is a wonderful food store in town (North Street Market), where you get olive oils from around the world, and flavored basalmic vinegars to different sea salts (pink, white, black). Don’t forget their yummy gelatos and wine bar.

    The Inn at Onancock is not the only inn in town. If you want more affordable choices, without sacrificing luxury try out the others. The Spinning Wheel has personable hosts and feels like home. The Inn and Garden won an award for their brunches. The 1882 Colonial Manor Inn has highly notable breakfasts and welcomes dogs and children. But the Manor is large enough that privacy and intimate romance is not impeded. Have morning coffee or evening wine in the beautiful gazebo overlooking the two acres of gardens.

    The added plus is that Onancock is centrally located in the middle of the Shore, which makes it a great base for seeing the rest of the Shore>

    I strongly urge at least a two night stay. One night is simply not enough to see Onancock.

      1. I did!! Well noted for their cream donuts and their sweet potato biscuits…everything made from scratch.

  9. My Children have several lots in Trails End, they rent very nice campers and at a great rate, just a short drive to Chincoteague….
    Clean comfortable fully stocked camper. Beautiful camping spot, with crabbing, fishing. See the ponies at the beach, shop in Chincoteague. Have a cozy fire in your fire pit, while you enjoy your steamed crabs and beer. Camping Resort has Olympic Pool, Restaurant with great food at very reasonable prices, nature trail, music and bands on many weekends, club house with crafts for the kids, large Play Ground, basketball court, soccer court, crabbing pier, Marina to launch your boat.

  10. Would love to show you an true beautiful oysters farm on your return. We are a grower for a wonderful company. We along with alot of growers produce one of the finest tasting oyster that goes all over the United states. We have been growing since 2010 and have watched the farm grow over a substantial a month due to the wonderful taste of the eastern shore oysters. Wonderful write up of the Eastern Shore. Thank you.

  11. Terry Mulligan Gross

    We loved Onancock and the Eastern Shore so much that we have decided to make it our permanent home now that we’ve retired! Regarding the Inn at Onancock the change of owners has not compromised the quality or service and the breakfasts are still scrumptious! The new owners have added a few extra touches that won’t disappoint!

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