Book a hotel near St. Michaels Winery, Downtown St. Michaels

Start date: Check-in selected.
To Date
End date: Check-out

Wander Wisely with exceptional service, 24/7 support

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Hotels near St. Michaels Winery

The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
Free cancellation
Reserve now, pay when you stay
0.79 km from St. Michaels Winery
The price is CA $245 per night
CA $245
CA $300 total
Jan 5 - Jan 6, 2026
includes taxes & fees
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. Popular attractions Higgins Yacht Yard and Marina and Muskrat Park are located nearby.
Breakfast included
Pet-friendly
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
1.1 km from St. Michaels Winery
Get rates
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. Popular attractions Perry Cabin Park and Higgins Yacht Yard and Marina are located nearby.
Pool
Hot tub
George Brooks House B&B

George Brooks House B&B

3 out of 5
24500 Rolles Range Road St. Michaels MD
1.87 km from St. Michaels Winery
The price is CA $209 per night
CA $209
CA $230 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Stay at this B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and St Michaels Nature Trail are located nearby.
Pool
Breakfast included
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free cancellation
1.88 km from St. Michaels Winery
The price is CA $129 per night
CA $129
CA $142 total
Jan 11 - Jan 12, 2026
includes taxes & fees
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 rooms in our reviews. Popular attractions Saint Michaels Village and Classic Motor Museum are located nearby.
Pool
Breakfast included
The Tilghman Island Inn

The Tilghman Island Inn

3.5 out of 5
21384 Coopertown Rd Tilghman MD
Free cancellation
Reserve now, pay when you stay
12.13 km from St. Michaels Winery
The price is CA $281 per night
CA $281
CA $309 total
Jan 18 - Jan 19, 2026
includes taxes & fees
Stay at this inn in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Tilghman Island Marina and Knapp's Narrows Marina & Inn are located nearby.
Pool
Breakfast included
Wylder Tilghman Island

Wylder Tilghman Island

2 out of 5
21551 Chesapeake Access Drive Tilghman MD
Free cancellation
Reserve now, pay when you stay
12.59 km from St. Michaels Winery
The price is CA $161 per night
CA $161
CA $238 total
Jan 6 - Jan 7, 2026
includes taxes & fees
Stay at this hotel in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tilghman Watermen’s Museum and Talbot County Library Tilghman Branch are located nearby.
On private beach
Pool
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Free cancellation
Reserve now, pay when you stay
12.83 km from St. Michaels Winery
The price is CA $245 per night
CA $245
CA $270 total
Jan 1 - Jan 2, 2026
includes taxes & fees
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 Avalon Theatre and Customs House are located nearby.
Spa
Parking included
Hampton Inn Easton

Hampton Inn Easton

2.5 out of 5
8058 Ocean Gateway Easton MD
Free cancellation
Reserve now, pay when you stay
14.02 km from St. Michaels Winery
The price is CA $160 per night
CA $160
CA $176 total
Jan 29 - Jan 30, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Easton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Easton Cycle and Sport and Easton Rail Depot are located nearby.
Pool
Breakfast included
Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG

3 out of 5
8561 Ocean Gateway Route 50 Easton MD
Free cancellation
14.08 km from St. Michaels Winery
The price is CA $185 per night
CA $185
CA $203 total
Jan 4 - Jan 5, 2026
includes taxes & fees
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 property condition in our reviews. Popular attractions Talbot Massage and Easton Cycle and Sport are located nearby.
Pool
Hot tub
Quality Inn

Quality Inn

2.5 out of 5
8523 Ocean Gtwy Easton MD
Free cancellation
Reserve now, pay when you stay
14.09 km from St. Michaels Winery
The price is CA $116 per night
CA $116
CA $128 total
Jan 6 - Jan 7, 2026
includes taxes & fees
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 in our reviews. Popular attractions Talbot Massage and Easton Cycle and Sport are located nearby.
Pool
Breakfast included
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 out of 5
8708 Alicia Drive Easton MD
Free cancellation
Reserve now, pay when you stay
14.18 km from St. Michaels Winery
The price is CA $163 per night
CA $163
CA $179 total
Jan 1 - Jan 2, 2026
includes taxes & fees
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 in our reviews. Popular attractions Talbot Massage and Easton Cycle and Sport are located nearby.
Pool
Parking included
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville MD
18.61 km from St. Michaels Winery
Get rates
Book a stay at this golf vacation home in Stevensville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and Northern Chesapeake Bay are located nearby.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in St. Michaels Winery
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.

About St. Michaels Winery Hotels Near Attractions

Do you have a full travel itinerary while visiting St. Michaels Winery? Don't waste your time commuting too far from St. Michaels Winery area attractions.

St. Michaels Winery hotels essential information

Accommodation
1,509 hotels
Lowest Price
CA $128
Highest Price
CA $309
Popular hotels
The Wildset, Inn at Perry Cabin, St Michaels Inn, George Brooks House B&B, The Tilghman Island Inn, Wylder Tilghman Island, The Tidewater Inn, Quality Inn, Best Western Plus Easton Inn & Suites, Hampton Inn Easton, Holiday Inn Express Easton by IHG, Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Recent St. Michaels Winery hotel reviews by fellow wanderers

Hampton Inn Easton

Hampton Inn Easton

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Nice room"
A verified traveller stayed at Hampton Inn Easton
Hampton Inn Easton

Types of hotels

Hotels near…

Areas of St. Michaels Winery