A waterfront street lined with trees and a white building with a balcony.

Find Romantic Hotels in St. Michaels, MD

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Check availability on St. Michaels Romantic Hotels

Tonight
29 Sep - 30 Sep
Tomorrow
30 Sep - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for St. Michaels romantic hotels

1. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
AED 327
AED 360 total
includes taxes & fees
6 Oct - 7 Oct
St Michaels Inn

2. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
AED 1,884
AED 2,073 total
includes taxes & fees
26 Oct - 27 Oct
Inn at Perry Cabin

3. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
William
AED 680
AED 747 total
includes taxes & fees
30 Sep - 1 Oct
The Tilghman Island Inn

4. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
AED 658
AED 724 total
includes taxes & fees
14 Oct - 15 Oct
The Tidewater Inn

5. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
United States
Amber
AED 992
AED 1,091 total
includes taxes & fees
30 Sep - 1 Oct
Sandaway Suites & Beach

6. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
AED 1,616
AED 1,778 total
includes taxes & fees
30 Sep - 1 Oct
The Oaks Waterfront

7. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
AED 479
AED 654 total
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort

8. Hummingbird Inn

Hummingbird Inn
Easton
United States
Ann
AED 1,088
AED 1,238 total
includes taxes & fees
30 Sep - 1 Oct
Hummingbird Inn

9. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Francine
AED 499
AED 676 total
includes taxes & fees
7 Oct - 8 Oct
Rod 'N' Reel Resort

10. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
United States
Danny B.
AED 331
AED 954 total
includes taxes & fees
8 Oct - 9 Oct
Cass-N-Reel Luxury Houseboat
View all properties

Find out more about St. Michaels

St. Michaels attractions for couples

St. Michaels, Maryland, is a charming retreat that invites families to explore its rich maritime heritage and stunning landscapes. Start your adventure at the Chesapeake Bay Maritime Museum, where interactive exhibits and beautiful waterfront views provide both education and entertainment for all ages. For some outdoor fun, hop on a bike and ride along the picturesque St. Michaels Nature Trail, where you can immerse yourself in the area's natural beauty while observing local wildlife. Don’t miss a scenic boat tour of the bay; these excursions offer a thrilling perspective on the region's history and breathtaking scenery. If you’re in the mood for a culinary experience, the local eateries, like the famous Crab Claw Restaurant, serve up fresh seafood that will delight your taste buds. For an exceptional stay, consider the historic inns and waterfront hotels, such as the Inn at Perry Cabin, where you can enjoy luxurious accommodations and attentive service, making your family feel pampered after a day of exploration. Each morning, wake up to stunning views and a delightful breakfast, setting the perfect tone for another day of adventure in this delightful town.

Find the best romantic hotels in St. Michaels

For couples seeking a romantic getaway in St. Michaels, Maryland, these hotels offer the perfect blend of charm and amenities to create unforgettable memories together.The Wildset

  • Why it's great for a couples retreat: The Wildset is a charming retreat perfect for couples looking to escape the everyday hustle. With an impressive review rating of 9.6, this hotel provides an inviting atmosphere that offers comfort and relaxation. Guests can enjoy luxurious touches such as Frette Italian sheets, designer toiletries, and cozy fireplaces in their rooms, making it an ideal spot for romantic evenings together.
  • Other amenities: In addition to its cozy accommodations, The Wildset features several appealing amenities, including free daily breakfast, concierge services, and complimentary self-parking. Guests can unwind on their private balconies or patios, and enjoy the resort-style housekeeping. Other features include a snack bar and gift shop, ensuring that all needs are met for a delightful stay.
  • Nearby attractions: Higgins Yacht Yard and Marina - 0.19 miles, Saint Michaels Town Hall - 0.21 miles, Muskrat Park - 0.26 miles

Inn at Perry Cabin

  • Why it's great for a couples retreat: For an upscale romantic retreat, the Inn at Perry Cabin stands out with its luxurious offerings and stunning waterfront views. With an exceptional review rating of 9.6, this hotel is perfect for couples looking to indulge in a lavish getaway. Guests can enjoy a pampering spa experience and unwind in the hot tub, while gourmet dining at the garden-view restaurant adds a touch of elegance to any evening.
  • Other amenities: Additional amenities include outdoor tennis courts, a heated outdoor pool, and golf lessons on-site, ensuring that guests can enjoy both relaxation and recreation. The Inn also offers 24-hour room service, valet parking, and a fitness center for those looking to maintain their routines. With beautifully furnished balconies and patios, as well as a full-service spa, every aspect of this hotel promotes romance and relaxation.
  • Nearby attractions: Perry Cabin Park - 0.07 miles, Higgins Yacht Yard and Marina - 0.42 miles, Saint Michaels Town Hall - 0.44 miles

Parsonage Inn

  • Why it's great for a couples retreat: Parsonage Inn is a delightful choice for couples seeking an intimate and cozy atmosphere. With an excellent review rating of 8.4, this inn features charming amenities that cater to romance, including terraces and private balconies where guests can enjoy peaceful moments together. The complimentary full breakfast sets the tone for a perfect day spent with loved ones.
  • Other amenities: In addition to its romantic offerings, the inn provides convenient amenities such as self-parking and daily housekeeping. Guests can unwind by the fireplace or explore the nearby historical district. The garden area and nearby museum add to the inn's allure, ensuring couples have plenty of options for exploration and relaxation during their stay.
  • Nearby attractions: Perry Cabin Park - 0.14 miles, Higgins Yacht Yard and Marina - 0.31 miles, Saint Michaels Town Hall - 0.32 miles

George Brooks House B&B

  • Why it's great for a couples retreat: George Brooks House B&B is a quaint and inviting bed and breakfast perfect for a romantic escape. With a review rating of 8.0, it offers a cozy atmosphere complemented by Victorian design elements that create a charming backdrop for couples. Guests can enjoy leisurely mornings with a delicious complimentary breakfast and relax by the outdoor pool.
  • Other amenities: The B&B boasts several appealing amenities, including self-parking, daily housekeeping, and a garden for serene strolls. Guests can unwind on furnished balconies or patios, adding to the romantic experience. The hotel also features electric car charging stations and a warm fireplace in rooms, enhancing comfort and convenience for travelers.
  • Nearby attractions: Perry Cabin Park - 0.45 miles, Higgins Yacht Yard and Marina - 0.91 miles, Saint Michaels Town Hall - 0.92 miles

St Michaels Inn

  • Why it's great for a couples retreat: St Michaels Inn is a lovely option for couples seeking a relaxed and romantic atmosphere. With a solid review rating of 8.0, it offers a cozy ambiance complemented by a refreshing pool and beautiful terrace spaces, perfect for enjoying sunset views together. The Inn’s inviting features create a serene escape for travelers.
  • Other amenities: Beyond its romantic setting, guests can take advantage of a variety of amenities, including free breakfast options, self-parking, and a garden area for leisurely strolls. The shared secured pool provides a perfect way to relax on warm days, while the close nearby shopping districts adds convenience for explorations. The Inn’s historical charm enhances the overall experience, making it a memorable stay for couples.
  • Nearby attractions: Saint Michaels Village - 0.57 miles, St. Michaels Winery - 1.18 miles, Classic Motor Museum - 1.28 miles

Top St. Michaels Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."
Tammy 2-night trip
Posted 4 hours ago
Annapolis Waterfront Hotel, Autograph Collection
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"This was a fabulous hotel. Staff was excellent very helpful. We used the shuttle to go to historic downtown. Very prompt picking us up. The drivers were so helpful and very kind. A perfect hotel to stay at especially having a shuttle not having to park in the busy historic area. The best staff we have seen at hotels."
Joyce 1-night trip
Posted 4 hours ago
DoubleTree by Hilton Hotel Annapolis
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Beautiful location. Indoor pool is fabulous."
Carolyn 5-night trip
Posted 2 days ago
Hyatt Regency Chesapeake Bay
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 8 days ago
The Westin Annapolis

Frequently asked questions

Searching for romantic hotels in St. Michaels?
Are you and your partner in need of a romantic getaway? Our guests also enjoy St. Michaels for its historic landmarks, shopping, and seafood restaurants. If you want to explore the area, you might head to St. Michaels Marina, Chesapeake Bay Maritime Museum, or St. Michaels Winery. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to St. Michaels?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in St. Michaels: The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for St. Michaels is 53 inches.
What is there to do in St. Michaels?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all that St. Michaels has to offer. Couples looking for a little of everything will enjoy St. Michaels for its historic landmarks, shopping, and seafood restaurants. You might think about visiting St. Michaels Marina, Chesapeake Bay Maritime Museum, or St. Michaels Winery.
What's the best way to get to St. Michaels and around town during my romantic getaway?
These transportation options in St. Michaels might help your romantic trip go off without a hitch: To get to St. Michaels, book a flight to Easton, MD (ESN-Easton - Newnam), which is the closest major airport, located 8.8 mi (14.1 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.

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