St. Michaels Winery Tours

They say you can't buy happiness, but at least you can buy amazing wine! Spend an afternoon discovering the quality products crafted by passionate local winemakers at St. Michaels Winery.

When you've finished exploring this wine-making establishment in St. Michaels, why not make your way to Chesapeake Bay Maritime Museum, and St. Michaels Museum? They're close to St. Michaels Winery and also a hit with many tourists.

Plan a trip to see St. Michaels Winery

Price found within the past 48 hours. Click for updated prices.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Price was $550, price is now $412 per person
$412
per person
Oct 2 - Oct 6
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Salisbury (SBY)
9.8/10 Exceptional! (278 reviews)
A great location for this beachy vibe motel. A couple things I would suggest to the property manager would be to offer a coffee cart each morning, add an additional chair and bedside table to the room and finally, I would suggest that the room be serviced automatically if you’re there for 4 nights…we didn’t get our room serviced our entire time. Beyond those minor things, it was a quirky, clean, convenient motel that has 95% of the components needed for a top-notch beach motel.

Reviewed on Aug 24, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,506, price is now $1,162 per person
$1,162
per person
Oct 2 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (3,117 reviews)
We stayed in OC many times. This hotel is way nicer than most of the other options. I would definitely recommed it and stay here again. The hotel had places to eat but there werent many shops or resturants nearby to walk to. Although, It is nicer to stay in this area than by the bussier part of the boardwalk. Staff was great. Our tv was broke and they came to replace it immediately. I will say the balcony was different. You can see everyone out on their balcony. Kind of awkward when you wanted to sit outside and neighbor was out on their balcony also. But, we were not in the room often for it to be an issuse. My family love it and said it looked like the best hotel there!

Reviewed on Aug 26, 2025

Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

2.5 out of 5
Downtown Ocean City
Price was $1,519, price is now $1,185 per person
$1,185
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
9/10 Wonderful! (1,005 reviews)
Nice in the beach get what you pay for

Reviewed on Aug 26, 2025

Popular places to visit

Chesapeake Bay Maritime Museum

Chesapeake Bay Maritime Museum

4.5/5(15 reviews)

You can study the exhibits at Chesapeake Bay Maritime Museum, a museum with a storied past, during your trip to St. Michaels. Stroll along the waterfront or experience the area's museums.

Chesapeake Bay Maritime Museum

Windon Distilling

You can take time to visit Windon Distilling during your travels to St. Michaels. Stroll along the waterfront or visit the shops in this romantic area.

Windon Distilling

Classic Motor Museum

You can spend time studying the exhibits at Classic Motor Museum during your travels in St. Michaels. Visit the shops in this romantic area, or simply enjoy its seafood restaurants.

Classic Motor Museum

St. Michaels Museum

You can browse the exhibits at St. Michaels Museum, a museum with a storied past, during your trip to St. Michaels. Discover the seafood restaurants and its museums while you're in the area.

St. Michaels Museum

Saint Marys Square

Saint Marys Square is just one of the places to see in St. Michaels, so why not enjoy the other things to explore during your travels? Stroll along this romantic area's waterfront, or simply enjoy its seafood restaurants.

Saint Marys Square

Saint Marys Square Museum

You can spend time browsing the exhibits at Saint Marys Square Museum during your trip to St. Michaels. Stroll along the waterfront or visit the shops in this romantic area.

Saint Marys Square Museum

Best Lodging Options Near St. Michaels Winery

The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
The Wildset
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
Inn at Perry Cabin
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
St Michaels Inn
Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street, St. Michaels, MD
Parsonage Inn
Sandaway Suites & Beach

Sandaway Suites & Beach

3 out of 5
103 West Strand Road, Oxford, MD
Sandaway Suites & Beach
Wylder Tilghman Island

Wylder Tilghman Island

2 out of 5
21551 Chesapeake Access Drive, Tilghman, MD
Wylder Tilghman Island
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St, Easton, MD
The Tidewater Inn
The Tilghman Island Inn

The Tilghman Island Inn

3.5 out of 5
21384 Coopertown Rd, Tilghman, MD
The Tilghman Island Inn
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road, Tilghman, MD
Knapps Narrows Marina & Inn
See all 1,558 properties in St. Michaels Winery
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.

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