Exclusive St. Michaels Winery Vacation Deals

St. Michaels Winery vacation package deals

Price found within the past 48 hours. Click for updated prices.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $673, price is now $624 per person
$624
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A garden is also provided.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,009, price is now $857 per person
$857
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's pool. Enjoy the 2 outdoor pools and perks like free self parking and free WiFi.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $877, price is now $760 per person
$760
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $758, price is now $671 per person
$671
per person
Feb 26 - Mar 2
found 6 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,319, price is now $1,211 per person
$1,211
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $904, price is now $832 per person
$832
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Dine at the beachfront restaurant and relax with beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with volleyball.

Frequently asked questions

How much are vacation packages to St. Michaels Winery?
If you like the idea of hassle-free planning and impressive savings, our $624 St. Michaels Winery vacation package will be right up your alley. With your flights and hotels sorted, organizing your trip around this well-loved attraction has never been more simple.
Where can I get the best vacation package deals for St. Michaels Winery?
It's simple — browse Travelocity. With 400 airlines and 1,000,000 properties around the world, it's easy to craft a St. Michaels Winery package deal that fits your budget.
Why should I purchase my St. Michaels Winery vacation bundle via Travelocity?
From enticing destinations to one-of-a-kind experiences, we have everything you need to appease your wanderlust. Our 24/7 customer support will also ensure you're taken care of before, during and after your trip. And don't fret if you notice a better price on your reservation, we'll match it. That's our Price Match Guarantee.

Top St. Michaels Winery hotel deals

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
$517 nightly
The price is $568 total per night
$568 total
Dec 23 - Dec 24
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room childcare. Enjoy the 3 outdoor tennis courts and perks like free valet parking and free WiFi.
Pool
Hot Tub
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $230 total per night
$230 total
Dec 21 - Dec 22
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a snack bar/deli, and concierge services are also on offer.
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free Cancellation
$95 nightly
The price is $105 total per night
$105 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.
Pool
Breakfast included
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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.