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

Find Romantic Hotels in St. Michaels, MD from CA $638

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on St. Michaels Romantic Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for St. Michaels romantic hotels

1. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
United States
barbara s.
CA $1,061
CA $1,868 total
includes taxes & fees
Oct 18 - Oct 19
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

2. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
United States
David R.
CA $990
CA $1,780 total
includes taxes & fees
Oct 19 - Oct 20
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

3. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
United States
Nancy N.
CA $354
CA $675 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 2br home w/ parking in downtown Annapolis

4. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
United States
Jill R.
CA $427
CA $638 total
includes taxes & fees
Nov 5 - Nov 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean room, very nice decor and great staff"
Nadine 2-night trip
Posted 16 hours ago
Graduate by Hilton Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"First time staying at the resort. We stayed two nights to celebrate my wife's birthday. I had ordered flowers that were delivered before our arrival and frontbdesk had them delivered to our room. The views from the waterfront tower build were amazing. The entire resort is very clean and well maintained. Good choice of restaurants/bars on site. Other restaurants are walkable or a short drive. The casino was surprisingly quiet and very clean, relaxing way to pass some time and maybe win some money. Enjoyed walking though the railroad museum that is on site as well. Everyone on this property were friendly and helpful. Will definitely return!"
James 2-night trip
Posted 17 hours ago
Rod 'N' Reel Resort
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"my stay went very well. the room was very clean and pleasant. the staff helped me with a couple of items, and the breakfast staff in the restaurant was extremely friendly and helpful."
PATRICK 3-night trip
Posted 17 hours ago
DoubleTree by Hilton Hotel Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 18 hours ago
St Michaels Inn
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."
Lamont 3-night trip
Posted 2 days ago
The Inn at Chesapeake Bay Beach Club
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

8/10 Good
"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"
Andrea 3-night trip
Posted 4 days ago
Hilton Garden Inn Annapolis Downtown
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 5 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.

Explore a world of travel with Expedia