your retreat by the river
welcome to
the chesapeake inn
in urbanna
Indulge yourself with a stay at our elegant, easy-going family- and pet-friendly inn near Washington, D.C., Richmond and the Chesapeake Bay! Tucked away in the heart of Urbanna, our chic little inn is the perfect romantic getaway, retreat spot, or personal sanctuary from the stresses of day-to-day life.
Relax in style in one of the recently redecorated and renovated guest rooms… enjoy the luxurious lobby, peaceful garden, and on-site restaurant… shop at Ballgown Barefoot, our stylish gift and home decor boutique… celebrate in the Rappahannock Room… explore Urbanna’s restaurants and shops, beautiful countryside and inviting waterways in complimentary kayaks and signature surrey carriages…
The Chesapeake Inn is family-owned and operated, and we take pride in providing each of our guests with true personalized hospitality — extra special treatment at no extra charge. Let us help you create your own retreat by the river!
X0XO Gari & Matt
your rooms
Each of the Inn’s 12 rooms is unique but all capture our signature coastal elegant style. We’ve renovated and reimagined our rooms to be brighter, lighter, and grander, with sparkling chandeliers, vibrant colors, vintage and modern furnishing, and raised beadboard ceilings reminiscent of Southern front porches. Original art carefully curated by Gari decorate the walls, and luxury amenities and plush towels adorn the bathrooms. Style does not mean sacrificing convenience, however: every room has high-speed wifi, cable TV, refrigerator, microwave, coffee maker and more. Relax and enjoy a stylish stay!
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your retreat ... your way
Escape the stresses of daily life to relax, reflect and recharge – whatever that means to you! Build just the retreat you want and need with fun, inspiring and even enriching experiences. . .
Kayak the creek… unwind in a sound bath… sip wine and taste local fresh oysters… bike or walk quiet historic streets… find strength and serenity in a yoga class… sway to live music… connect with horses during a coached Equus session… watch for eagles and dolphins… explore antique shops… or just lounge with a paperback in the private garden…
Enjoy seafood the Urbanna way — one night with a sophisticated flight of oysters at sunset on the Rappahannock at Merroir . . . the next night shuck crabs at a picnic table over the water at the Urbanna Seafood Bar & Grill.
Upcoming Happenings
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April 24 at 5pm and April 25 at 7:30pm
This is your chance to witness one of the last traditional tent shows left in America. Their mission is to provide children of all ages with the opportunity to experience the magic of the circus.
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This event has become one of the largest gatherings of plein air painters in the state! Come out to watch award winning painters working on locations throughout Middlesex County.
Events will be held throughout the week, including painting demonstrations and art exhibitions.
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Urbanna Second Saturday
May 11, 9am-1pmThe Urbanna Farmer’s Market is held every second Saturday all summer in Taber Park. Enjoy food trucks and music by Rein Radio Rocks as you shop!
Stock up on home grown and homemade goodies: choice flower arrangements, just-picked produce, fresh baked goods, artisanal cheeses, clothing, jewelry, soaps, candles and a special section just for local artists.
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Urbanna’s newly renovated public pool reopens Memorial Day weekend! Thanks to the updates, the pool and bathhouse are ADA accessible, and a new snack bar offers delicious after-swim treats.
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June 1 from 10am-5pm
June 2 from 10am-3pmVoted a Best Art Event by Virginia Living Magazine, the Arts in the Middle festival features fine artists from across the country that exhibit and sell their creations in a variety of mediums on the beautifully restored Hewick Plantation. One hundred-plus artists and over a dozen music groups will be featured throughout the weekend.
Admission to the festival and parking is free!
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Urbanna Second Saturday
June 8 , 9am-1pmThe Urbanna Farmer’s Market is held every second Saturday all summer in Taber Park. Enjoy food trucks and music by Julius Pittman Project as you shop!
Stock up on home grown and homemade goodies: choice flower arrangements, just-picked produce, fresh baked goods, artisanal cheeses, clothing, jewelry, soaps, candles and a special section just for local artists.
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Enjoy Urbanna’s 4th festivities at Taber Park with food trucks, patriotic music, games and free swimming for all at the new town pool.
No ticket or registration is required.
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Urbanna Second Saturday
July 13, 9am-1pmThe Urbanna Farmer’s Market is held every second Saturday all summer in Taber Park. Enjoy food trucks and music by Sweet Justice as you shop!
Stock up on home grown and homemade goodies: choice flower arrangements, just-picked produce, fresh baked goods, artisanal cheeses, clothing, jewelry, soaps, candles and a special section just for local artists.
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Presented by the Friends of Urbanna annually since 2014, this event celebrates Urbanna’s colonial history and presents educational programs for all. including performances and historical games.
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Urbanna Second Saturday
August 10, 9am-1pmThe Urbanna Farmer’s Market is held every second Saturday all summer in Taber Park. Enjoy food trucks and music by Game Changers as you shop!
Stock up on home grown and homemade goodies: choice flower arrangements, just-picked produce, fresh baked goods, artisanal cheeses, clothing, jewelry, soaps, candles and a special section just for local artists.
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Urbanna Second Saturday
September 14, 9am-1pmThe Urbanna Farmer’s Market is held every second Saturday all summer in Taber Park. Enjoy food trucks and music by Tequila Sunrise as you shop!
Stock up on home grown and homemade goodies: choice flower arrangements, just-picked produce, fresh baked goods, artisanal cheeses, clothing, jewelry, soaps, candles and a special section just for local artists.
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November 1 from 10:00am to 8:00pm
November 2 from 9:00am to 5:00pmJoin us for the 67th annual Urbanna Oyster Festival
Enjoy over 50 food vendors & every kind of oyster, as well as live music and beer and wine tastings. The festival is fun for the whole family with arts and crafts, an antique auto show, and children's activities spread throughout the town. The town marina offers historical boats and exhibits on the conservation of the Chesapeake Bay, watermen and the oyster industry.
chessie’s promise
At the Chesapeake Inn, you are our priority. We’re committed to “Chessie’s Promise,” which is named after our beloved border collie and inn namesake. We believe in:
personalized hospitality
predictable pricing
pampering
a plethora of experiences
guest reviews
your urbanna
The Chesapeake Inn is nestled in the heart of Urbanna, a small picturesque town of less than 500 residents that dates to 100 years before the American Revolution. The historic port town hugs the Rappahannock River and is surrounded by waterways perfect for boating, kayaking and exploring, including the River, Urbanna Creek and Dragon Run. The area around Urbanna is brimming with wildlife: Urbanna is a bird sanctuary, and it is not unusual to see eagles and osprey overhead and dolphins and stingray in the waterways.
And the food . . . delicious BBQ, fresh Mexican ,and of course the best seafood around. Whether it’s a margarita under an umbrella at Mi Jalesco, homemade blackberry ice cream at Something Different, pizza with all the toppings at Angelo’s, delicious fried oysters at Little Jimmy’s or a lobster roll at Small Town Burger, you can have it all in Urbanna.
Urbanna hosts Virginia’s official annual Oyster Festival every November, but offers family-friendly adventures, dining, shopping, site-seeing, and water sports all year round. Visit and enjoy Urbanna for all seasons!
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celebrate with us
We love celebrations of all shapes and sizes! Whether you want us to help with something traditional or something more unusual or complex, we are here to help! We’ve sourced key lime pie and Eton Mess and we love decorating guest rooms for birthdays and anniversaries. We can’t promise we can find everything, but we do promise we will move mountains and do our very best to make miracles happen!
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family & pet friendly
Create family memories with us! Kids love it here - between the yard games in our Garden, the surreys and the bikes, our welcome gift bags and library of toys, there is always something fun to do. Parents love that we don’t charge for our stash of baby supplies, and everyone loves how family and dog friendly Urbanna is. Take the kids or your pup kayaking or reserve a boat trip. Bike to the town’s playground or hop on the Pearl trolley for a ride to our favorite spot for miniature golf and ice cream.
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group retreats, reunions & weddings
Let us host your group! Our rooms and public spaces are well-designed to give guests privacy and yet lots of space for collegial get-togethers, whether a day of meetings in the Rappahannock Room, cocktails in the living room, a cookout on the Garden, a morning-after brunch or a meeting in the conference room. Let us help you plan a midweek retreat for your company or a weekend away for your family!