Downtown St. Michaels Vacation Packages for 2026

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Top Hotel Deals

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
0.62 km from Downtown St. Michaels
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

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
0.37 km from Downtown St. Michaels
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

Parsonage Inn

3.5 out of 5
210 North Talbot Street St. Michaels MD
0.43 km from Downtown St. Michaels
Stay at this B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Higgins Yacht Yard and Marina and Muskrat Park are located ...
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
29.05 km from Downtown St. Michaels
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
28.88 km from Downtown St. Michaels
Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and ...
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5
3101 Main Street Grasonville MD
20.43 km from Downtown St. Michaels
Book a stay at this business-friendly hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
2.25 km from Downtown St. Michaels
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 ...
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road Stevensville MD
23.2 km from Downtown St. Michaels
Book a stay at this spa hotel in Stevensville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S Grasonville MD
20.5 km from Downtown St. Michaels
Book a stay at this business-friendly hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3 out of 5
3206 Main St Grasonville MD
20.23 km from Downtown St. Michaels
Book a stay at this business-friendly hotel in Grasonville. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
30.31 km from Downtown St. Michaels
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. ...
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

2.5 out of 5
101 Vfw Ave Grasonville MD
19.8 km from Downtown St. Michaels
Stay at this hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Cambridge Inn

Cambridge Inn

2 out of 5
2831 Ocean Gateway Cambridge MD
29.93 km from Downtown St. Michaels
Stay at this hotel in Cambridge. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Bay Country Shop and Dorchester County Historical ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Jul 11 - Wed, Jul 15
PHL
Philadelphia Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$419 Roundtrip, found 10 hours ago
$419
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Jul 11 from Philadelphia Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Jul 15, priced at $419 found 10 hours ago
American Airlines
Sat, Sep 26 - Tue, Sep 29
BOS
Logan Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$452 Roundtrip, found 1 day ago
$452
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 26 from Logan Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Sep 29, priced at $452 found 1 day ago
American Airlines
Sat, Jul 11 - Wed, Jul 15
PHL
Philadelphia Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$463 Roundtrip, found 10 hours ago
$463
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Jul 11 from Philadelphia Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Jul 15, priced at $463 found 10 hours ago
American Airlines
Sat, Jul 11 - Wed, Jul 15
PHL
Philadelphia Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$509 Roundtrip, found 10 hours ago
$509
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Jul 11 from Philadelphia Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Jul 15, priced at $509 found 10 hours ago