Search Deals onSt. Michaels Winery Vacation Packages
St. Michaels Winery Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

The Americana Hotel
Price was $701, price is now $572 per person
$572
per person
Oct 11 - Oct 15
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, a beach locale, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

The Lodge at Great Oak Landing
Price was $793, price is now $643 per person
$643
per person
Oct 15 - Oct 20
found 7 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive are located nearby.

Boardwalk One
Price was $675, price is now $575 per person
$575
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star beach aparthotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Americana Princess Suites and Condos
Price was $1,454, price is now $1,251 per person
$1,251
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
Book a stay at this business-friendly condo in Ocean City. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Bethany Beach Ocean Suites Residence Inn by Marriott
Price was $1,293, price is now $977 per person
$977
per person
Oct 11 - Oct 15
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star beach hotel in Bethany Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bethany Beach Boardwalk and Bethany Beach Bandstand are located nearby.

Grand Hotel Ocean City Oceanfront
Price was $943, price is now $782 per person
$782
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star beach hotel in Ocean City. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the pool and the restaurant in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

OCHG Townhouse 102 10
Price was $1,676, price is now $1,393 per person
$1,393
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star condo in Ocean City. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Sahara Motel
Price was $734, price is now $615 per person
$615
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this motel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Ocean 1 Hotel and Suites
Price was $808, price is now $694 per person
$694
per person
Oct 11 - Oct 15
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

OCHG Beachviews
Price was $1,089, price is now $941 per person
$941
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Ocean City Beach and Ocean City Boardwalk are located nearby.

Miramar Condominiums
Price was $1,608, price is now $1,389 per person
$1,389
per person
Oct 11 - Oct 15
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Beach Walk
Price was $692, price is now $607 per person
$607
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
3-4 Night Vacations in St. Michaels Winery
Price found within the past 48 hours. Click for updated prices.



5-7 Night Vacations in St. Michaels Winery
Price found within the past 48 hours. Click for updated prices.



St. Michaels Winery Last Minute Hotel Deals

St Michaels Inn
1228 S Talbot Street, St. Michaels, MD
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Inn at Perry Cabin
308 Watkins Ln, St. Michaels, MD
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...

The Wildset
209 N Talbot St, St. Michaels, MD
Stay at this hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...

Parsonage Inn
210 North Talbot Street, St. Michaels, MD
Stay at this 3.5-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and Higgins Yacht Yard and ...

George Brooks House B&B
24500 Rolles Range Road, St. Michaels, MD
Stay at this 3-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and St Michaels Nature Trail ...

The Tidewater Inn
101 E Dover St, Easton, MD
Stay at this 3-star spa hotel in Easton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions ...

Sandaway Suites & Beach
103 West Strand Road, Oxford, MD
Stay at this 3-star beach guesthouse in Oxford. Enjoy free WiFi, free parking, and a private beach. Our guests praise the property condition in our reviews. ...

The Tilghman Island Inn
21384 Coopertown Rd, Tilghman, MD
Stay at this 3.5-star inn in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
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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