Downtown St. Michaels Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Inn at Perry Cabin

Inn at Perry Cabin

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

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

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 ...
St Michaels Inn

St Michaels Inn

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 ...
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

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

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 Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

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 ...
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

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 ...
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

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. ...
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

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 ...
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

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 ...
The Tidewater Inn

The Tidewater Inn

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 ...
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

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. ...
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

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 ...
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

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. ...
Don't see what you're looking for?
See all available properties in Downtown St. Michaels
View all properties
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
American Airlines
American Airlines
Breeze Airways
Sun, Oct 4 - Wed, Oct 7
PSM
Portsmouth Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$644
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Sun, Oct 4 from Portsmouth Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Oct 7, priced at $644 found 20 hours ago