Top St. Michaels Hotel Deals

Make the Most of Your St. Michaels Stay

A maritime legacy preserved

St. Michaels earned its nickname "The Town That Fooled the British" during the War of 1812, when residents allegedly hung lanterns in trees to misdirect cannon fire. Today, this waterfront enclave on Maryland's Eastern Shore preserves that maritime heritage through Federal and Victorian architecture lining the harbor, where the economy once thrived on shipbuilding and oystering. The 18-acre Chesapeake Bay Maritime Museum anchors the experience with its working boatyard, historic vessels, and the restored 1879 Hooper Strait Lighthouse.

Refined waterfront dining and stays

The culinary scene reflects the town's evolution into an upscale destination, with Stars at the Inn at Perry Cabin delivering sophisticated waterfront dining focused on Chesapeake seafood, while Ruse at The Wildset Hotel offers modern American cuisine sourcing from local watermen. The Inn at Perry Cabin, built in 1816 by a War of 1812 veteran, provides luxury accommodations on 26 acres along the Miles River, featuring a Pete Dye golf course and spa. Talbot Street's walkable mile connects boutique shopping with waterfront activities.

Practical considerations

Most visitors arrive via rental car from BWI Airport, 70 miles away. The compact downtown rewards exploration on foot. Nearby Easton offers additional dining and arts, while Tilghman Island provides authentic waterman culture just 15 minutes away. The Oxford-Bellevue Ferry creates a scenic route to historic Oxford.

Frequently Asked Questions about St. Michaels

Can I book hotels in St. Michaels on Delta Stays using miles?

Yes, you can use your Delta miles for your hotel reservation in St. Michaels, or you can opt for a miles-plus-cash combination to provide more booking options. When you log in to your Delta SkyMiles® account, you will also discover Member offers at select properties that could enhance your travel experience.

What are the benefits if I use Delta Stays to book my hotel stay in St. Michaels?

As a SkyMiles Member, you will earn 2 miles per $1 spent on completed hotel stays and vacation rentals reserved through Delta Stays. Plus, you will receive access to Member promotions at select properties, along with the option to complete payment using miles, cash, or a combination. Simply sign in to your SkyMiles account or enter your SkyMiles number at checkout when paying with cash to ensure you earn your miles. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

What is the policy to change or cancel my hotel booking made through Delta Stays?

Cancellation policies vary by property. We recommend reviewing the specific cancellation policy displayed under each hotel's details before completing your reservation. You will notice that refundable options are available for some rates, while others may be non-refundable. Any modifications or cancellations to your reservation may affect the number of miles you earn and receive in your account.

Can my Delta SkyMiles® American Express® Card be used for booking?

As a Delta SkyMiles® Gold, Platinum, or Reserve American Express® Cardholder, you enjoy the advantage of earning additional miles alongside numerous valuable benefits, including an annual statement credit of up to $200 applicable toward prepaid accommodations booked through Delta Cars and Stays. These offers are subject to specific terms. If you would like to explore all the benefits available with your card, please visit the Delta SkyMiles® American Express Credit Cards page for complete details.

Can I earn MQDs on Delta Stays hotel bookings?

From time to time, Delta Stays may present special opportunities for SkyMiles Members to earn Medallion® Qualification Dollars on their hotel and vacation rental bookings made through Delta Stays. We recommend accessing the Delta Stays MQD Offer page to view current MQDs promotions and examine their terms and conditions.

In order to book a hotel on Delta Stays, do I need to be a Delta SkyMiles Member?

No, Delta Stays is available to everyone for hotel bookings. However, by becoming a SkyMiles Member, you will unlock the ability to earn miles and access Member-only prices and offers. As a Member, you will earn 2 miles per $1 you spend on Delta Cars and Stays (excluding taxes and additional charges). Plus joining SkyMiles is free. Register today by visiting the delta.com.

Can I book a vacation rental through Delta Stays?

Yes, beyond traditional hotels, Delta Stays provides an extensive collection of vacation rentals for your travel needs. You can search for homes, condos, and other unique stays powered by Vrbo on the Vacation Rentals page.

Which hotels have good ratings in St. Michaels?

Inn at Perry Cabin has a guest rating of 9.6 out of 10, and features an outdoor pool and a hot tub. Another top-rated bed & breakfast is Parsonage Inn, where you can enjoy a free full breakfast and proposal/romance packages.

What's a good time of year to visit St. Michaels?

To experience St. Michaels during great weather, consider a visit in September when the temperature averages in the 70s and the skies are mostly sunny with lower humidity. For off-peak prices and more deals on hotels, consider visiting during January when temperatures are cold with moderately low visitor numbers and greater availability.

Which hotels in St. Michaels are located near Chesapeake Bay Maritime Museum?

The Chesapeake Bay Maritime Museum brings bay history to life through its working shipyard where you can watch skilled shipwrights restore traditional vessels and climb the 1879 lighthouse. Inn at Perry Cabin is a popular hotel, which is just steps away. Another top hotel is The Oaks Waterfront and it is within a short drive.

Which hotels in St. Michaels are near St. Michaels Winery?

Sample Maryland's Eastern Shore wines at St. Michaels Winery, where 18 handcrafted varieties showcase the region's unique terroir in the historic Old Mill District. Popular hotels include Inn at Perry Cabin which is a 15-minute walk. Another top hotel is The Oaks Waterfront and it is within a short drive.

Which hotels in St. Michaels are located closest to 1879 Hooper Straight Lighthouse?

This rare screwpile lighthouse, relocated from Chesapeake Bay, invites you to climb the spiral staircase to the lantern room for sweeping views and a glimpse into 19th-century keeper's life. One popular hotel is Inn at Perry Cabin which is steps away. The Oaks Waterfront is another well-reviewed hotel and it is within a short drive.

Are there any luxury 4-star and 5-star hotels in St. Michaels?

St. Michaels offers many notable luxury hotels. At Inn at Perry Cabin, guests love the outdoor pool. To explore luxury stays in other destinations, visit the Luxury Stays page.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar