The Chesapeake Inn - Jamaica

Two-Night Stay at The Chesapeake Inn in Urbanna, VA

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Cozy Inn Nestled Along Tributary of Chesapeake Bay

The Chesapeake Inn, a venerable brick building, sits within walking distance of the shores of a Chesapeake Bay tributary. The inn’s decor frequently references the nearby bay: upon entering, you’ll see a cluster of wooden oars poking out of a wooden barrel, as if they were stowed there by a fisherman freshly arrived from a day on the water. Across the hall, two pieces of driftwood have been repurposed as lamps. They bookend a large painting of a weathered rowboat set in a gilded frame.

Thirteen unique rooms populate the inn; their coastal decor includes framed maps and tiny sailboats. There’s a full-size refrigerator and microwave for midnight snacking.

White wicker furniture dots the outdoor courtyard, which overlooks a tiny pond adorned with wildlife sculptures. The front-desk staff rents surrey bicycles at no charge⎯they’re a convenient way to see downtown Urbanna and the Rappahannock River area without strapping a webcam to a seagull.

Urbanna, Virginia: Tranquil Coastal Town Rife with History

Urbanna was founded in 1680 as a port town nestled along the Rappahannock River, a tributary that feeds into Chesapeake Bay. According to legend, Patrick Henry once addressed the townspeople from the steps of a pub on Prince George Street. The tiny waterfront community packs a lot into a half-square-mile package, including a number of restaurants, a historical district, and special events such as the annual Urbanna Oyster Festival.

About an hour's drive away, Jamestown Settlement re-creates the historic colony via a living-history museum, costumed characters, and gallery exhibits. Patrons can board replicas of the three English ships that crossed the Atlantic in 1607, explore the re-created James Fort, or visit a simulated Powhatan village. Relics of the real settlement can be explored in nearby Jamestown, which features excavated ruins of the actual colonial site.

Read the Fine Print for important info on travel dates and other restrictions.

What You Get

Two-night stay for two in any room

  • $169, valid for arrival Wednesday, Thursday, or Friday (up to a $338 total value)

Book by: 3/22/13
Travel by: 4/28/13

Read the Fine Print for important info on travel dates and other restrictions.


  • Outdoor courtyard 
  • Individually decorated rooms with deluxe bedding 
  • Full-size refrigerators 
  • Complimentary cookies and coffee
  • Free WiFi
  • Complimentary bike rentals
  • On-site restaurant, Ostra Raw Bar and Grill

The Fine Print

  • Must book by 3/22/13 or promotional value expires. Must complete travel by 4/28/13
  • Limit 2 per person, may buy 2 additional as gifts
  • Limit 2 per visit
  • Reservation required, subject to availability
  • 48hr cancellation notice required or fee up to Groupon price applies
  • Must be 18 or older to check in
  • Credit card required at booking and check-in
  • 10% tax not included.

Other Details

Room Details

  • One king bed or two queen beds 
  • Standard occupancy: 2 
  • Maximum occupancy: 4
  • Adding occupants above standard: $25 for each additional guest 18 or older; additional guests 17 or younger are free
  • Full-size refrigerator
  • LCD flat-screen TV

Hotel Policies

  • Check in: 3 p.m.
  • Check out: 11 a.m.
  • Parking: free
  • Rollaways: available for an additional $15 fee per day
  • Smoking policy: no smoking inside the property
  • Pet policy: pets are not allowed inside the property.
  • Accessibility: handicap-accessible rooms are not available. 
  • Room upgrades: not available

Getting There

  • By plane: about 52 miles from Richmond International Airport (RIC)
  • By car: about 58 miles east of Richmond, VA

Traveler's Tips

  • Visit for information on local dining, shopping, and events.
  • On-site restaurant, Ostra Raw Bar and Grill, is closed 1/23-2/6 and 2/27-3/6

Customer Reviews

(189 ratings)

100% Verified Reviews
All reviews are from people who have redeemed deals with this merchant.


Daniele B. ·
May 22, 2013
Nicely decorated rooms, walking distance to the shops and restaurants in Urbanna. Nice starting point for exploring the surrounding areas including Gloucester and Irvington. Really cute tandem bicycles available for guest use. Great way to explore the town. Very kid friendly.


Jan H. ·
May 3, 2013
Everything was great! Nice staff, lovely ambiance, location perfect, food outstanding!


Brenda B. ·
April 18, 2013
The Chesapeake Inn was wonderful. Sadly we were not able to stay two nights because the twins just wouldnt sleep BUT we enjoyed our one. The place looks great, is super clean, love the decore, too many wonderful things about it to put in this space. I have recommended it to all of my friends and raved about it to anyone who I have spoken to since our visit. I was disappointed in the fact there were not high chairs for the kids in the restaurant. Our intentions were to eat there. It was on our list of things to do. Well we were told how great your brunch is so waited and adjusted schedules (baby naps) in order to have brunch there. That is my only complaint. Other than that one problem the stay was good. Sorry it had to be cut short.
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