In This Article

Want a relaxing couple’s escape without going too far? These weekend getaways in Maryland for couples offer cozy inns, waterfront charm, and scenic spots perfect for reconnecting.

Highlights:

  • Romantic stays in historic Annapolis
  • Seaside charm in St. Michaels
  • Winery tours along the Chesapeake Wine Trail
  • Cozy mountain cabins in Deep Creek Lake
  • Scenic strolls and seafood dining on the Eastern Shore

Unique Weekend Getaways in Maryland for Couples:

1. Rod 'N' Reel Resort - 1 hour 10 minutes from Baltimore

Rod 'N' Reel Resort - 1 hour 10 minutes from Baltimore

© Rod 'N' Reel Resort

Location:

Chesapeake Beach, MD

Highlights:

If you're looking for a versatile getaway with a bit of everything, we highly recommend Rod 'N' Reel Resort in Chesapeake Beach. Whether you're after family fun, a relaxing retreat, or exciting adventures, this waterfront resort has you covered!

Recommended For:

Families, couples, wedding parties, and anyone seeking a fun-filled, scenic escape on Maryland’s waterfront.

What I Love: ♥

The mix of exciting activities, waterfront views, and top-notch amenities like a relaxing spa and entertaining games.
  • Stay in one of 72 cozy rooms and suites, with some offering stunning waterfront views.
  • Relax at the rejuvenating spa or enjoy some time in the casino game rooms.
  • Explore exciting marina water activities, or catch an entertaining concert during your stay.
  • Dine at one of the three tempting restaurants, including the Rod 'N' Reel Restaurant, serving fresh Southern Maryland seafood.

Address:

Rod 'N' Reel Resort, 4165 Mears Avenue, Chesapeake Beach, MD 20732
Phone: 866-312-5596

2. Wylder Hotel, Tilghman Island - 1 hour 50 min

Wylder Hotel, Tilghman Island - 1 hour 50 min

© Wylder Hotel

Location:

Tilghman Island, MD

Highlights:

If you’re seeking a peaceful escape on the water, we recommend Wylder Hotel on Tilghman Island. Nestled on a charming 3-mile island in Chesapeake Bay, this boutique hotel offers a tranquil, nature-filled getaway with plenty of activities to enjoy.

Recommended For:

Couples, nature lovers, and anyone wanting to unwind and experience the beauty of Chesapeake Bay.

What I Love: ♥

The combination of outdoor activities like kayaking and sunset cruises, plus the rustic charm of a historic hotel.
  • Relax around the salt-water pool or enjoy a peaceful day on the island.
  • Explore the island by kayak, paddle-board, or bicycle, and enjoy some bocce ball along the way.
  • Experience a fishing charter or take a romantic sunset cruise for a truly unforgettable day.
  • Dine at Tickler’s Crab Shack and Bar Mumbo, where you can enjoy craft cocktails and fresh seafood.

Address:

Wylder Hotel on Tilghman Island, 21551 Chesapeake House Dr, Tilghman, MD 21671
Phone: 410-886-2121

3. Annapolis Waterfront Hotel

Annapolis Waterfront Hotel

© Annapolis Waterfront Hotel

Location:

Annapolis, MD

Highlights:

If you're looking for a romantic waterfront escape, we highly recommend Annapolis Waterfront Hotel. This Marriott Autograph Collection hotel offers couples the perfect place to relax, unwind, and explore the scenic Annapolis Harbor.

Recommended For:

Couples, water sports enthusiasts, history lovers, and anyone seeking a romantic getaway in Maryland.

What I Love: ♥

The serene atmosphere, stunning harbor views, and close proximity to attractions like Annapolis Historic Downtown and "The Yard."
  • Relax in rooms with calming décor and brilliant views, creating the perfect environment for unwinding.
  • Explore nearby attractions like Annapolis Historic Downtown and "The Yard," just steps from the hotel.
  • Dine at Pusser’s Caribbean Grille, which serves delicious Caribbean fare right on-site.
  • Enjoy sailing and other water sports, with the hotel’s prime location along Annapolis Harbor.

Address:

Annapolis Waterfront Hotel, 80 Compromise Street, Annapolis, MD 21401
Phone: 410-268-7555

Luxury Weekend Getaways in Maryland for Couples:

4. St. Michaels Harbour Inn, Marina and Spa - 1 hour 30 minutes from Baltimore

St. Michaels Harbour Inn, Marina and Spa - 1 hour 30 minutes from Baltimore

© The Harbour Inn

Location:

St. Michaels, MD

Highlights:

If you're looking for a peaceful waterfront retreat, we highly recommend St. Michaels Harbour Inn, Marina & Spa. Located in the heart of Chesapeake Bay, this inn offers the perfect blend of relaxation, water activities, and charming local attractions.

Recommended For:

Couples, families, or anyone seeking a scenic, relaxing getaway with easy access to shopping, antiquing, and waterfront dining.

What I Love: ♥

The serene waterfront views, deluxe accommodations, and the combination of rejuvenating spa treatments and delicious dining options.
  • Stay in one of 49 deluxe rooms, including 32 light-filled suites with beautiful views of the Bay.
  • Relax with a daily continental breakfast, complete with an omelet bar, and enjoy the complimentary shuttle service.
  • Explore the area on one of the hotel’s bicycles or simply unwind by the water.
  • Dine at The Harbourside Grill, where you can enjoy lunch, dinner, and cocktails with unforgettable views of the Bay.
  • Soothe your senses at the Spa at Harbour Inn with indulgent treatments like body wraps and massages.

Address:

101 N. Harbor Rd, St. Michaels, Maryland 21663
Phone: 410-745-9001

5. The Reynolds Tavern - 35 minutes

The Reynolds Tavern - 35 minutes

© The Reynolds Tavern

Location:

Annapolis, MD

Highlights:

For a truly historic and luxurious stay, we recommend Reynolds Tavern in Annapolis. As one of the oldest taverns in the United States, this charming bed and breakfast offers a unique blend of history, comfort, and elegance.

Recommended For:

History buffs, couples, and anyone looking to experience a cozy yet luxurious stay steeped in tradition.

What I Love: ♥

The rich history, beautifully restored rooms, and the opportunity to indulge in the classic High Tea experience daily.
  • Stay in one of three refined two-room suites, decorated with gorgeous antiques, exquisite oriental rugs, and cozy bedding.
  • Relax in the historic setting, with original hardwood floors, staircases, and a center hall that remains largely unchanged since its 1747 design.
  • Dine in the Reynolds Tavern restaurant, offering delicious food in a rich, historic ambiance.
  • Indulge in the daily High Tea experience, a must-do tradition for guests.

Address:

7 Church Circle, Annapolis, Maryland 21401
Phone: 410-295-9555

6. Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore

Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore

© Hyatt Regency Chesapeake Bay

Location:

Cambridge, MD

Highlights:

If you're looking for a family-friendly escape or a romantic retreat, we recommend Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina. This expansive 400-acre resort offers stunning views of the Choptank River and a wealth of amenities for everyone.

Recommended For:

Families, couples, golf enthusiasts, and anyone seeking a peaceful getaway with plenty of activities and luxurious relaxation options.

What I Love: ♥

The wide range of recreational activities, indulgent spa treatments, and fantastic dining options for every taste.
  • Stay in one of the resort’s luxurious rooms or suites, all equipped with a refrigerator, microwave, cable TV, and free Wi-Fi.
  • Dine at any of the seven onsite restaurants, each offering diverse dining experiences.
  • Golf at the River Marsh Golf Club, or enjoy a friendly match on the resort’s tennis courts.
  • Relax in the indoor and outdoor pools, perfect for unwinding after a busy day.
  • Soothe your senses at Sago Spa and Salon with indulgent pampering treatments.

Address:

Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina, 100 Heron Blvd. at Route 50, Cambridge, Maryland, 21613
Phone: 410-901-1234

7. Wisp Resort

Wisp Resort

© Wisp Resort

Location:

McHenry, MD

Highlights:

If you're seeking an adventure-filled getaway, we highly recommend Wisp Resort. Nestled in the western mountains of Maryland, this year-round resort offers skiing, golfing, and endless outdoor fun for all ages.

Recommended For:

Skiers, golfers, outdoor enthusiasts, and couples looking for a romantic or action-packed getaway.

What I Love: ♥

The diverse range of activities, from skiing on 172 acres of slopes to enjoying the stunning 18-hole Lodestone Course, plus the cozy accommodations and dining options.
  • Stay in one of 102 suites or 67 deluxe guest rooms, each equipped with a refrigerator, microwave, coffee maker, cable TV, and complimentary Wi-Fi.
  • Ski down over 100 inches of snow on 172 acres of slopes during winter, or enjoy a mountain game of golf on the beautiful Lodestone Course in the warmer months.
  • Dine at six on-site dining options, including the rustic DC’s Bar & Restaurant, serving breakfast, lunch, and dinner.
  • Relax in a cozy suite or room that feels like a true mountain home away from home.

Address:

296 Marsh Hill Road, McHenry, Maryland 21541
Phone: 301-859-3159

8. Gaylord National Resort

Gaylord National Resort

© Gaylord National Resort

Location:

National Harbor, MD

Highlights:

If you’re looking for luxury with stunning views, we recommend Gaylord National Resort in National Harbor. From the lobby atrium, you’ll be treated to breathtaking views of the Potomac River and Washington, D.C., making it a perfect blend of relaxation and sightseeing.

Recommended For:

Couples, families, wellness enthusiasts, and anyone seeking a luxurious stay with proximity to Washington, D.C.

What I Love: ♥

The expansive fitness center, world-class spa treatments, and panoramic views from the Pose Rooftop. Plus, the variety of dining options makes it a true culinary destination.
  • Stay in deluxe rooms or suites, some of which offer stunning views of the atrium or the Potomac River.
  • Relax in the 20,000-square-foot fitness center, complete with a pool, cardio equipment, and free weights.
  • Soothe your body with luxurious treatments at Relâche Spa, including wraps, massages, scrubs, and facials.
  • Dine at one of the six fabulous on-site restaurants, including The Pose Rooftop, which boasts floor-to-ceiling windows and unbeatable views of Washington, D.C.

Address:

Gaylord National Resort, 201 Waterfront Street, National Harbor, Maryland 20745
Phone: 301-965-4000

9. The Columbia Inn at Peralynna

The Columbia Inn at Peralynna

© The Columbia Inn at Peralynna

Location:

Columbia, MD

Highlights:

If you’re looking for a peaceful, luxurious retreat, we highly recommend Columbia Inn at Peralynna. Nestled in the rolling hills of Columbia, Maryland, this elegant boutique hotel provides a tranquil setting for romantic getaways, business trips, and intimate weddings.

Recommended For:

Couples, business travelers, those planning corporate retreats, and anyone seeking a peaceful, upscale escape.

What I Love: ♥

The boutique charm, luxurious amenities, and the personalized, intimate atmosphere that feels like staying in a high-end bed and breakfast.
  • Stay in one of the 17 uniquely decorated rooms and grand suites, each offering a distinct style.
  • Relax in the four-story Great Room, equipped with games, movies, and books for your enjoyment.
  • Indulge in made-to-order breakfasts daily, featuring pastries that will leave you craving more.
  • Unwind with wine, cheese, and crackers in the atrium, while taking in spectacular views of the surrounding area.
  • Explore the Renaissance rooms, decorated with timeless antiques and replicas, transporting you to another era.

Address:

Columbia Inn at Peralynna, 10605 State Route 108, Columbia, Maryland 21044
Phone: 410-715-4600

10. Great Oak Manor, Maryland

Great Oak Manor, Maryland

© Great Oak Manor

Location:

Chestertown, MD

Highlights:

If you’re looking for a peaceful retreat with a touch of sophistication, we highly recommend Great Oak Manor. This 18th-century country-style bed and breakfast on Chesapeake Bay offers the perfect blend of relaxation, history, and beautiful surroundings.

Recommended For:

Couples, history lovers, and anyone seeking a tranquil, scenic getaway on the Eastern Shore.

What I Love: ♥

The inviting atmosphere, the opportunity for outdoor adventure, and the stunning views of the Chesapeake Bay that can be enjoyed while relaxing at the manor.
  • Stay in one of the 12 elegant suites, each featuring plush towels, feather beds, and luxurious bath amenities.
  • Relax in cheerily decorated common rooms, where you can socialize, read, or enjoy freshly prepared snacks, coffee, or tea.
  • Explore the Eastern Shore on bicycles or paddleboards available for guests.
  • Indulge in a fresh homemade breakfast each morning, with stunning views of the bay as you dine.

Address:

10568 Cliff Rd, Chestertown, Maryland 21620
Phone: 410-778-5943

Frequently Asked Questions:

  • Q: What types of accommodations are available for a weekend getaway in Maryland?
  • A: Maryland offers a variety of accommodations, from charming country inns to full-service resorts, providing great options for a relaxing weekend getaway.
  • Q: Where can visitors enjoy romantic water views in Maryland?
  • A: Visitors can head to Chesapeake Bay or National Harbor to enjoy romantic water views, a wide choice of restaurants, and exciting activities.
  • Q: What can guests expect from a stay at a historic inn?
  • A: Checking into a historic inn surrounded by nature offers a tranquil setting where guests can rejuvenate with great food and friendly service.

Driving Distances from Baltimore

From Baltimore To Driving Time
Chesapeake Beach1 hour 10 minutes
Easton1 hour 15 minutes
North Beach1 hour 15 minutes
St. Michaels1 hour 30 minutes
Annapolis35 minutes
Cambridge1 hour 30 minutes
Mchenry3 hours 10 minutes
National Harbor55 minutes
Columbia20 minutes
Chestertown1 hour 30 minutes
Oxford1 hour 40 minutes
Annapolis35 minutes
Stevenson20 minutes
Catonsville15 minutes
Flinstone2 hours
Oakland3 hours

Plan Your Trip