A harbor with boats docked, a pier, and a row of houses along the water.

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Check availability on Chesapeake Beach Romantic Hotels

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Oct 3 - Oct 4
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Oct 4 - Oct 5
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Oct 9 - Oct 11
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Oct 16 - Oct 18

Our top choices for Chesapeake Beach romantic hotels

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

1. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Francine
NT$4,607
NT$6,174 total
includes taxes & fees
Oct 12 - Oct 13
Rod 'N' Reel Resort
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A waterfront property with a dock, a sailboat, and a building with a red roof.
A large building with a swimming pool, dock, and green surroundings.
A modern lounge area with a fireplace, seating, and a view of the outdoors.

2. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
William
NT$5,894
NT$6,484 total
includes taxes & fees
Oct 5 - Oct 6
The Tilghman Island Inn
A two-story building with a covered entrance and an American flag.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A hotel room with two beds, a chair, and a painting on the wall.

3. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
NT$2,839
NT$3,123 total
includes taxes & fees
Oct 5 - Oct 6
St Michaels Inn
A room with a white door, a wooden coat rack with robes, a lamp, and a bottle on a side table.
Front of property
A person holding a shark tooth in a room with a staircase, a red chair, and patterned carpet.
A driveway leading to a parked convertible car with an American flag on the side.

4. Historic 1825 Chesapeake Farm Stay

Historic 1825 Chesapeake Farm Stay
St. Leonard
United States
Theresa
NT$4,258
NT$4,727 total
includes taxes & fees
Oct 19 - Oct 20
Historic 1825 Chesapeake Farm Stay
A hot tub in a grassy area with a building in the background.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A pool with two Adirondack chairs and a basket of items on the grass.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.

5. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
James
NT$11,146
NT$12,706 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Tacaro Estate
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".
A hotel reception area with a reception desk, a television, and seating area.
A hotel pool area with two pools, chairs, and a sunshade.

6. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Lisa
NT$4,110
NT$4,685 total
includes taxes & fees
Nov 2 - Nov 3
SpringHill Suites by Marriott Annapolis
A room with a view of a wooden deck and a gazebo by the water.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A hotel room with a large bed, a chair, a desk, and a television.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

7. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
NT$16,345
NT$17,979 total
includes taxes & fees
Oct 26 - Oct 27
Inn at Perry Cabin
A patio area with outdoor seating, a fire pit, and a poolside bar.
A Marriott Residence Inn with a parking lot and a landscaped area.
A spacious lobby with a fireplace, comfortable seating, and a large television.
A hotel with a swimming pool, outdoor seating, and a brick facade.

8. Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf
Waldorf
United States
Nelson
NT$3,494
NT$3,878 total
includes taxes & fees
Nov 1 - Nov 2
Residence Inn by Marriott Waldorf
A lakeside view with sailboats, grassy areas, and white Adirondack chairs.
A bottle of Merlot wine and two glasses on a wooden tray by a window overlooking a lake.
A beach with clear water, sandy shore, and some vegetation.
A waterfront bar with outdoor seating, a view of the water, and American flags.

9. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
United States
Amber
NT$9,557
NT$10,513 total
includes taxes & fees
Oct 6 - Oct 7
Sandaway Suites & Beach
View all properties

Find out more about Chesapeake Beach

Chesapeake Beach attractions for couples

Chesapeake Beach, Maryland, is a charming coastal town that offers a wealth of activities and points of interest for families seeking quality experiences. Start your adventure at the Chesapeake Beach Water Park, where the kids can splash around in the wave pool and zoom down thrilling water slides while you relax in a cabana. For a taste of local history, visit the Calvert Marine Museum, where interactive exhibits and a chance to see live otters make learning exciting for all ages. Nature lovers will enjoy the beautiful hiking trails at the nearby Ward Farm Recreation and Nature Park, perfect for a family picnic amidst lush greenery. Don’t miss the chance to indulge in fresh seafood at local favorites like The Rod 'N' Reel, where you can dine with stunning views of the Chesapeake Bay. Finally, unwind at one of the town’s waterfront hotels, such as the Chesapeake Beach Resort & Spa, where spacious rooms and attentive service create a pampering retreat after a day of exploration. Here, you can rejuvenate at the spa or sip cocktails by the beach, making your family getaway both relaxing and memorable.

Find the best romantic hotels in Chesapeake Beach

For couples seeking a romantic escape in Chesapeake Beach, Maryland, these charming hotels offer perfect settings and amenities to enhance your getaway experience.Rod 'N' Reel Resort

  • Why it's great for a couples retreat: For a romantic getaway that combines beachside charm with modern comforts, Rod 'N' Reel Resort is an excellent choice. With a guest review rating of 8.2, this resort provides a cozy ambiance perfect for couples. Guests can unwind together at the beachfront restaurant or enjoy a relaxing day by the indoor pool. The resort also features lovely partial ocean and marina views, enhancing the romantic atmosphere throughout your stay.
  • Other amenities: Additional amenities include an onsite spa for rejuvenating treatments, pool cabanas for private lounging, and evening entertainment to enjoy together. Couples can take advantage of the boat tours or nearby kayaking for a more adventurous outing. Other features such as 24-hour fitness facilities, a sauna for relaxation, and cozy fireplaces in select rooms create a perfect blend of comfort and romance, ensuring a memorable stay.
  • Nearby attractions: Chesapeake Beach Railway Museum - 0.07 miles, Rod n Reel Charter Fishing - 0.08 miles, Chesapeake Beach Water Park - 0.28 miles

Top Chesapeake Beach Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 2 days ago
St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."
Christina 2-night trip
Posted 4 days ago
Inn at Perry Cabin
Wingate by Wyndham Waldorf/Washington DC Area

Wingate by Wyndham Waldorf/Washington DC Area

8/10 Good
"Una falta grave, contraté cinco habitaciones triples y cuando llegué solo habían dos camas por habitación y no hubo respuesta favorable de parte del hotel cuando se le reclamó, eso es un engaño."
Anselmo Bautista 1-night trip
Posted 5 days ago
Wingate by Wyndham Waldorf/Washington DC Area

Frequently asked questions

Searching for romantic hotels in Chesapeake Beach?
If you and your partner need a romantic escape, we'd like to help you plan for it. Our guests also enjoy Chesapeake Beach for its restaurants and beaches. If you'd like to explore some of the area's notable sights, you might make a stop by Chesapeake Beach Water Park, Chesapeake Beach Railway Museum, or Rod n Reel Charter Fishing. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chesapeake Beach?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chesapeake Beach: 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 40°F. Average annual precipitation for Chesapeake Beach is 52 inches.
What is there to do in Chesapeake Beach?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Chesapeake Beach has to offer. If you and your partner are interested in sampling the area's cuisine, you'll enjoy Chesapeake Beach for its restaurants. A visit to Chesapeake Beach Water Park, Chesapeake Beach Railway Museum, or Rod n Reel Charter Fishing might be just the ticket when you're checking out the sights.
What's the best way to get to Chesapeake Beach and around town during my romantic getaway?
These transportation options in Chesapeake Beach might help your romantic trip go off without a hitch: Make your way to Chesapeake Beach with a flight to Easton, MD (ESN-Easton - Newnam), which is the closest major airport located 26.5 mi (42.7 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

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