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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Arts in the Middle is returning for Arts at the Inn, at the Chesapeake Inn in Urbanna! Over 15 artists are exhibiting this year. The pop up gallery will be open November 30th to December 2nd, with an opening reception on the night of the 1st.
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The famous Urbanna Christmas parade is now an all-day family event. It begins with “Breakfast with the Elves,” features a pet parade, and finishes with the spectacular Christmas parade. In between you’ll find alpacas, Christmas crafts for kids, wine tastings, a festival of trees and more - including a visit from Santa Claus at the Urbanna firehouse!
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Dec. 9, 11am-4pm
Celebrate the holidays strolling through some of Urbanna’s most notable, historic and beautiful homes, all decked out for the season! From the regal Rosegill plantation overlooking the Rappahannock River, to the recently renovated town tavern, to the quirky Little Key House, to the stately Lansdowne estate on Urbanna’s main street. This year’s Urbanna’s Holiday Home Tour builds on a tradition started in 1985 by Urbanna Beautification Inc. (UBI) to raise funds for lampposts, artwork and other town enhancements. Urbanna Main Street, a local volunteer community revitalization initiative, is joining with UBI to host this year’s home tour.
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Visit with Santa Claus at Little Jimmy’s from 9 to noon.
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Boarding times 5, 6:30 & 8 pm each day
Climb into your toastiest PJs, grab your Golden Ticket and come aboard the Urbanna Polar Express. Get ready for a journey to the North Pole with magical stops full of surprises and meet your favorite characters along the way. Santa and Mrs. Claus will be waiting at the North Pole for all Believers!
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Make a reservation to dine with the Grinch at Something Different.
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 delicious drink on the Harbor at Portside Grill, homemade blackberry ice cream at Something Different, delicious fried oysters at Little Jimmy’s or a fabulous burger at BigOak Cafe, 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!