An elegant, easy-going retreat for couples, families and pets nestled in an historic port town.
4.8
An elegant, easy-going retreat for couples, families and pets nestled in an historic port town.
4.8
BOOK NOW
BOOK NOW
The Basics
SELECT REGISTRY MEMBER SINCE 7/17/2025
Nestled in the heart an historic port town, The Chesapeake Inn is the perfect romantic getaway, retreat spot, or personal sanctuary from the stresses of day-to-day life. Our chandeliered rooms, picturesque garden, lovely lobby, surprising store, and sumptuous spa, sauna and studio all reflect an elegant, easy-going style. We pride ourselves in providing personalized hospitality. Families and pets most welcome, delicious oysters and local cuisine steps away, and surreys and kayaks free of charge!
In the Know
Enjoy the best bivalves on the Bay at the home of Virginia's official annual Oyster Festival, 75 years running!
Explore the Rappahannock River, historic Urbanna Creek, or nearby Dragon Run with the inn's complimentary kayaks!
Behold the famous Mitchell Map that helped settle the Revolutionary War, housed at the Urbanna Scottish Factor Store Museum!
Wander the small town streets, coastal parks, and local bird sanctuaries on one of the inn's signature four-wheeled surreys!
Stay for the Story
D.C. natives Gari and Matt bought The Chesapeake Inn in 2020 because they believed everyone needs a special place to escape the chaos of daily life. They've built an elegant, easy-going retreat where guests can truly unwind.
Sip & Savor
Here are a few things to sip & savor when you visit…
Somethin' Different offers pit-smoked meats, specialty sandwiches, and other hearty options, all made from scratch with fresh, quality ingredients.
Fine Mexican cuisine and jumbo frozen margaritas await at family-owned Mi Jalisco, one of Urbanna's hottest spots.
Try a flight of amazing Steamboat Wharf top-shelf oysters and a local brew or wine at Urbanna Pearl Oyster Tavern, a new local favorite!
See & Do
Here are a few things to see & do when you visit…
Find curated moments of beauty, love and delight for your home, wardrobe and life at Ballgown Barefoot, Urbanna's newest design destination!
Charter a picnic lunch sail or sunset cruise on the Rappahannock River aboard a sporty catamaran docked in Urbanna just a short stroll from the inn!
Book a private yoga class, sauna, spa treatment, or Equus session through the Barefoot Studio, Sauna and Spa at The Chesapeake Inn!
Guest Reviews
⭐⭐⭐⭐⭐ Absolutely fabulous! I’m a total hotel snob, and this place exceeded all my expectations. Everything was perfect. The staff was genuinely warm and accommodating. The rooms were super clean and beautifully kept. The location could not be better, and you can tell they truly care about the guest experience. It is rare that I walk away from a stay with zero complaints, but this one nailed it. Five...See More
- J P
Beautifully designed and appointed, robes and free snacks in your room were a nice touch. It's very quiet despite being in the center of town. Gorgeous garden area with many options for seating. Free use of bicycles too.
- Leigh Simmons
We just completed our second stay at The Chesapeake Inn, and it won’t be our last. Everything about this place is charming, welcoming, and wonderful. Highlights are the decor, both in the rooms and the expansive lobby, the welcome basket of snacks, newspaper, and water, and the lovely handwritten note from the proprietors. Highly recommend!
- Lisa Stylos
The Chesapeake Inn is a hidden gem in Urbanna, VA. I can’t say enough good things about this little Inn. Our room was beautifully appointed with crisp white linens, comfy armchairs, and the cutest decor. It even had a beautiful chandelier and recessed lights. The lobby looked like a showroom for an interior decorator and the grounds are peppered with settees with colorful throw pillows. Everything about this little...See More
- Henrietta Beightol
We stayed for my husband's 60th birthday. I gave a five star because I couldn't give a 10. ????The owners went out of their way to make us feel special, and cannot give them enough praise for their hospitality. Thank you! We hope to see you again. Lisa
- Lisa Brindle
Rooms & Suites
# of Rooms: 12
Room Amenities: Air Conditioning, Bathrobes, Coffee Maker/Service, Hair Dryer, Rollaway Available, USB Charging Stations, Alarm Clocks, Antique Furnishings
Explore Rooms & SuitesFor information on ADA accessibility for the facility or its rooms, please contact the property directly.
Policies
Smoking Policy: Outside Only
Family Friendly: Yes
Learn moreFrequently Asked Questions
Does The Chesapeake Inn in Urbanna, VA offer free parking for guests?
Yes, we offer free onsite parking.
Are spa services like massage available during a stay at The Chesapeake Inn?
Yes, spa services are available including yoga, sauna, spa treatments, and Equus sessions.
Can The Chesapeake Inn accommodate dietary restrictions for breakfast?
Yes, special diets are accommodated.
What room features are offered at The Chesapeake Inn in Urbanna, VA (fireplaces, soaking tubs, porches)?
Rooms may include jetted tubs, private entrances, antique furnishings, air conditioning, smart TVs, coffee makers, and bathrobes.
Does The Chesapeake Inn have a restaurant, bar, or lounge onsite?
No, there’s no restaurant onsite.
What are the best nearby restaurants for lunch or dinner close to The Chesapeake Inn in Urbanna, VA?
Here are a few favorite local spots near the inn:
• Somethin’ Different – Pit-smoked meats, specialty sandwiches, and hearty homemade meals.
• Mi Jalisco – Family-owned spot with fine Mexican cuisine and jumbo margaritas.
• Urbanna Pearl Oyster Tavern – Fresh oysters, local brews, and a lively tavern atmosphere.
Are pets allowed at The Chesapeake Inn in Urbanna, VA?
Yes, pets are welcome.
What is the cancellation policy at The Chesapeake Inn in Urbanna, VA?
Please see our detailed policy here: https://www.thechesapeakeinn.com/cancellation-policy
Is The Chesapeake Inn family-friendly, and do you allow children?
Yes, we welcome families and children.
How many guest rooms or suites are at The Chesapeake Inn in Urbanna, VA?
We have 12 guest rooms.
What makes The Chesapeake Inn unique compared to other places to stay in Virginia’s Southeast Region?
Owned by Gari and Matt since 2020, the inn blends historic charm with an elegant, easy-going retreat style where guests can unwind with personalized hospitality.
Is The Chesapeake Inn in Urbanna, VA accessible for guests with disabilities?
Accessibility is limited.
Does The Chesapeake Inn support sustainable travel (eco-friendly practices, EV charging)?
Yes, we support eco-friendly practices, though EV charging is not listed.
Can you host weddings, elopements, or private events at The Chesapeake Inn in Urbanna, VA?
Yes, we host weddings, elopements, receptions, rehearsal dinners, bridal luncheons, baby showers, and private parties with both indoor and outdoor facilities.
What are the top attractions near The Chesapeake Inn in Urbanna, VA?
Guests often ask about nearby attractions. Here are some highlights:
• Ballgown Barefoot – A boutique design destination.
• Nauticat Charters – Picnic lunch sails or sunset cruises on the Rappahannock River.
• Barefoot Studio & Spa – Private yoga, sauna, and spa experiences.
Insider Tips
• Urbanna hosts Virginia’s official Oyster Festival each year.
• Explore Urbanna Creek and Dragon Run with complimentary kayaks.
• See the historic Mitchell Map at the Scottish Factor Store Museum.
• Ride around town in one of the inn’s signature surreys.
How far is The Chesapeake Inn in Urbanna, VA from the nearest major city or airport?
Urbanna is about 65 miles (1.5 hours) from Richmond International Airport (RIC) and 85 miles (2 hours) from Norfolk International Airport (ORF).
Food & Wine
Restaurant on Premises: No
Dining Amenities: Complimentary Early Coffee Tea, Complimentary Snacks
Explore Food & WineGuest Services
Internet Service: Wireless
Front Desk/Security: Business Hours
Inn Amenities: Concierge Services, Free Onsite Parking, Gardens on Property, LGBTQI+ Friendly, Meeting Space Available, Spa Service, Weddings & Events Available
Explore Guest ServicesWeddings & Celebrations
Wedding/Reception/Event Facilities: Indoor, Outdoor
Events Supported: Private Parties, Ceremonies, Receptions, Rehearsal Dinners, Bridal Luncheons, Elopements, Baby Showers, Tea Parties
Explore Event SpaceBusiness Travel & Meetings
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