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 ...
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 ...
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. ...
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 ...
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 WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 out of 5
8708 Alicia Drive Easton MD
14.24 km from Downtown St. Michaels
Book a stay at this business-friendly hotel in Easton. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and 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. ...
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 ...
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
12.94 km from Downtown St. Michaels
Book a stay at this 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 ...
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 out of 5
1020 Kent Narrows Rd Grasonville MD
20.67 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 helpful staff in our reviews. ...
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 ...
Quality Inn

Quality Inn

2.5 out of 5
8523 Ocean Gtwy Easton MD
14.17 km from Downtown St. Michaels
Book a stay at this business-friendly hotel in Easton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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 ...
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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
$394 Roundtrip, just found
$394
Roundtrip
just found
Select American Airlines flight, departing Sat, Jul 11 from Philadelphia Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Jul 15, priced at $394 just found
American Airlines
Sat, Jul 11 - Wed, Jul 15
PHL
Philadelphia Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$403 Roundtrip, just found
$403
Roundtrip
just found
Select American Airlines flight, departing Sat, Jul 11 from Philadelphia Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Jul 15, priced at $403 just found
American Airlines
Sat, Sep 26 - Tue, Sep 29
BOS
Logan Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$410 Roundtrip, found 5 hours ago
$410
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Sep 26 from Logan Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Sep 29, priced at $410 found 5 hours ago
Breeze Airways
Sun, Sep 27 - Fri, Oct 2
PSM
Portsmouth Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$669 Roundtrip, found 5 hours ago
$669
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sun, Sep 27 from Portsmouth Intl. to Salisbury - Ocean City Wicomico Regional, returning Fri, Oct 2, priced at $669 found 5 hours ago