Hotels near Cassinelli Winery and Vineyards Church Hill

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Where to stay near Cassinelli Winery and Vineyards?

Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (344)
The price is $76
includes taxes & fees
$68 per night
May 1 - May 2
Red Roof Inn & Suites Chestertown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other landmarks in Church Hill

Church Hill Theatre

You can enjoy a show at Church Hill Theatre during your trip to Church Hill.

See properties in Church Hill Theatre
Church Hill Theatre
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

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Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What are the best hotels near Cassinelli Winery and Vineyards?
  • Guests enjoy staying at The Lodge at Great Oak Landing, which is a lodge close to Cassinelli Winery and Vineyards.
  • Another highly rated lodge is Hilton Garden Inn Kent Island Marina, which is 35 minutes away by car.
  • In fact, you’ll have plenty of options to choose from with 1,420 hotels, vacation rentals, and other accommodation options in the area.
How much does it cost to stay in a hotel near Cassinelli Winery and Vineyards?
Visit Hotels.com, enter your search criteria, and sort by price to see the lowest rates. You’ll find a variety of room prices depending on when and where you plan to go.
  • Search for the lowest price per night $70
What cheap hotels are close to Cassinelli Winery and Vineyards?
Can I find hotels close to Cassinelli Winery and Vineyards that are fully refundable?
Yes, you’ll find hotels with refundable room rates, but be sure to check the cancellation deadline before you book. To find refundable rates, use the “Fully refundable” filter when you search for hotels.
What are the best romantic hotels near Cassinelli Winery and Vineyards?
  • For a romantic stay, Kent Island Resort offers an outdoor pool and couples/private dining. It’s a 41-minute drive from Cassinelli Winery and Vineyards.
  • Hummingbird Inn is another great choice, and it’s in the larger area.
What are the best hotels close to Cassinelli Winery and Vineyards with free breakfast?
Which hotels near Cassinelli Winery and Vineyards have rooms with great views?
What are the best family hotels close to Cassinelli Winery and Vineyards?
What are the best luxury hotels near Cassinelli Winery and Vineyards?
  • Pamper yourself with a stay at Inn at 202 Dover, which is within reach of Cassinelli Winery and Vineyards and has a restaurant called Peacock Restaurant where you can enjoy a convenient meal.
  • Another luxurious option is Inn at Perry Cabin, which is in the larger area.
What are the best hotels near Cassinelli Winery and Vineyards with free parking?
  • Drive and park with ease when you stay at Driftwood Inn, which offers free parking. You’ll be a short 17-minute drive from Cassinelli Winery and Vineyards.
  • Hillside Motel also has free parking and is 17 minutes away by car.
What are the best hotels near Cassinelli Winery and Vineyards with a pool?
  • If swimming is at the top of your list, The Colonial Farmhouse has an outdoor pool and a private pool. Cassinelli Winery and Vineyards is a short 15-minute drive from the hotel.
  • Another great choice for a hotel with a pool is Best Western Kent Narrows Inn.
What cheap motels can I book close to Cassinelli Winery and Vineyards?
  • To stay economically near Cassinelli Winery and Vineyards, you can book Mariners Motel, which offers an outdoor pool and parking.
  • Another inexpensive motel nearby to consider is Driftwood Inn.
What are the best things to see and do around my hotel near Cassinelli Winery and Vineyards?
  • While you’re here to visit Cassinelli Winery and Vineyards, you may also want to see nearby attractions like U.S. Naval Academy, Dover International Speedway, and Chesapeake Bay Bridge.
  • DE Turf Sports Complex, Annapolis City Dock, and Sandy Point State Park are other places to visit in the area.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

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