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

Find Romantic Hotels in St. Michaels, MD from CA $118

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Check availability on St. Michaels Romantic Hotels

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for St. Michaels romantic hotels

1. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Dean
CA $108
CA $118 total
includes taxes & fees
Nov 24 - Nov 25
St Michaels Inn

2. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
CA $679
CA $746 total
includes taxes & fees
Nov 11 - Nov 12
Inn at Perry Cabin

3. Parsonage Inn

Parsonage Inn
Downtown St. Michaels
United States
Paul
CA $350
CA $385 total
includes taxes & fees
Nov 3 - Nov 4
Parsonage Inn

4. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
Kelly
CA $245
CA $270 total
includes taxes & fees
Oct 28 - Oct 29
The Tilghman Island Inn

5. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
CA $616
CA $678 total
includes taxes & fees
Oct 28 - Oct 29
The Oaks Waterfront

6. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
CA $231
CA $254 total
includes taxes & fees
Nov 2 - Nov 3
The Tidewater Inn

7. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
United States
Gary
CA $410
CA $451 total
includes taxes & fees
Nov 24 - Nov 25
Sandaway Suites & Beach

8. Hummingbird Inn

Hummingbird Inn
Easton
United States
Todd
CA $415
CA $472 total
includes taxes & fees
Nov 2 - Nov 3
Hummingbird Inn

9. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
CA $171
CA $236 total
includes taxes & fees
Nov 16 - Nov 17
Kent Island Resort

10. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
John
CA $202
CA $269 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Regency Chesapeake Bay
View all properties

Find out more about St. Michaels

St. Michaels attractions for couples

St. Michaels, Maryland, is a charming waterfront town perfect for discerning travellers. Begin your exploration at the Chesapeake Bay Maritime Museum, where interactive exhibits dive into the region's rich nautical history, offering hands-on experiences that both children and adults will appreciate. Next, take a leisurely stroll along the picturesque streets lined with historic buildings and boutique shops, perhaps stopping for a local artisan coffee at a quaint café. For a taste of adventure, consider a guided kayak tour through the tranquil waters of the Bay, where you might spot playful dolphins and a variety of bird species. Don’t miss a visit to the St. Michaels Winery for a delightful afternoon of wine tasting, complete with local cheese pairings. For accommodation, the picturesque inns and hotels near the waterfront offer not only stunning views but also exceptional service; the Inn at Perry Cabin, for instance, features luxurious rooms and a relaxing spa, ensuring you feel pampered after a day of exploration. Enjoying your stay in this beautiful town means embracing both tranquillity and adventure, making memorable family experiences without sacrificing comfort.

Find the best romantic hotels in St. Michaels

St. Michaels offers a charming backdrop for romance, and these hotels provide the perfect setting for a romantic getaway, complete with intimate amenities and luxurious touches.The Wildset

  • Why it's great for a couples retreat: Why it’s great: The Wildset is an enchanting retreat that captures the essence of romance, with an impressive review rating of 9.8. With its inviting atmosphere and thoughtful amenities, travelers can enjoy complimentary breakfast and a serene stay with enchanting views from private balconies or patios, making it a perfect choice for couples looking to unwind together.
  • Other amenities:
  • Other amenities: Guests will appreciate the elegant Frette Italian sheets and premium bedding that ensure a restful night’s sleep. The hotel features complimentary housekeeping and concierge services, adding to the convenience of your stay. Additional highlights include a cozy fireplace, designer toiletries, and snack bar options, providing everything needed for a romantic escape.
  • Nearby attractions: Higgins Yacht Yard and Marina - 0.3 km, Saint Michaels Town Hall - 0.3 km, Muskrat Park - 0.4 km

Inn at Perry Cabin

  • Why it's great for a couples retreat: Why it’s great: A luxurious haven for couples, the Inn at Perry Cabin is a top choice for romantic getaways, with an exceptional review rating of 9.6. This upscale hotel features an outdoor pool and a full-service spa, providing the perfect environment for relaxation and pampering, ensuring a memorable experience for travelers seeking intimacy and indulgence.
  • Other amenities:
  • Other amenities: Guests can enjoy exquisite dining experiences with garden and ocean views at the onsite restaurant. The hotel also offers tennis courts, a hot tub, and various treatments at the spa, including manicures and aromatherapy. Romantic touches like a fireplace and deep soaking bathtubs in select rooms enhance the atmosphere of romance throughout your stay.
  • Nearby attractions: Perry Cabin Park - 0.1 km, Higgins Yacht Yard and Marina - 0.7 km, Saint Michaels Town Hall - 0.7 km

Parsonage Inn

  • Why it's great for a couples retreat: Why it’s great: The Parsonage Inn presents a delightful romantic escape with a fantastic review rating of 9.2. Couples will appreciate the charming decor and the complimentary full breakfast, perfect for starting each day together. With features like a terrace and garden, this inn offers an intimate setting for quiet moments.
  • Other amenities:
  • Other amenities: Guests can indulge in champagne service, enhancing the romantic experience. The hotel also includes air conditioning for comfort, along with self-parking facilities. Historical district access adds an exciting element for couples eager to explore, making it a lovely spot for a romantic getaway.
  • Nearby attractions: Perry Cabin Park - 0.2 km, Higgins Yacht Yard and Marina - 0.5 km, Saint Michaels Town Hall - 0.5 km

George Brooks House B&B

  • Why it's great for a couples retreat: Why it’s great: With its Victorian charm and a strong review rating of 8.8, George Brooks House B&B is a romantic haven for couples looking to create lasting memories. The homey atmosphere, combined with complimentary breakfast options, sets the stage for a delightful stay in a picturesque setting.
  • Other amenities:
  • Other amenities: Guests can enjoy the outdoor pool and beautiful garden areas, perfect for leisurely afternoon strolls. The inn also provides self-parking and comfortable furnishings, including premium bedding and bathrobes for added luxury. Its convenient location near local attractions allows couples to explore the quaint charm of St. Michaels together.
  • Nearby attractions: Perry Cabin Park - 0.7 km, Higgins Yacht Yard and Marina - 1.5 km, Saint Michaels Town Hall - 1.5 km

St Michaels Inn

  • Why it's great for a couples retreat: Why it’s great: With a warm and inviting atmosphere, St Michaels Inn is ideal for couples seeking a romantic retreat, backed by an excellent review rating of 8.2. Guests can indulge in a complimentary breakfast before strolling through the beautiful surroundings or relaxing by the shared outdoor pool, creating a serene and intimate setting for lovebirds.
  • Other amenities:
  • Other amenities: The hotel features a lovely terrace and garden area, perfect for quiet moments together. Additional offerings include self-parking and air conditioning for comfort. The convenient access to the historical district and shopping adds an extra layer of charm, allowing couples to explore the local culture hand-in-hand.
  • Nearby attractions: Saint Michaels Village - 0.9 km, St. Michaels Winery - 1.9 km, Classic Motor Museum - 2.1 km

Top St. Michaels Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Easy access to downtown, Great waterside restaurants."
John 1-night trip
Posted 12 hours ago
Annapolis Waterfront Hotel, Autograph Collection
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Great last minute booking. All went smoothly"
Kelly 1-night trip
Posted 1 day ago
The Westin Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."
William 1-night trip
Posted 1 day ago
Rod 'N' Reel Resort
Best Western Annapolis

Best Western Annapolis

8/10 Good
"If you want to get a feel for Annapolis, you should try a hotel closer to the harbor. Since we had seen Annapolis many times and were looking for a quick, efficient stay, this met our needs. A few remarks on the property; - Needs updates -bathroom door did not close fully - mystery eggs were part of breakfast, but coffee was good."
David 1-night trip
Posted 1 day ago
Best Western Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"older facility but kept clean. a good value for an over night"
John 1-night trip
Posted 1 day ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Very pleasant surprise! Great price for studio apartment- way better than the Marriott I just checked out of!"
Rhonda 1-night trip
Posted 2 days ago
Sonesta ES Suites 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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