25 Best Weekend Getaways in Maryland for Couples

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

Rod 'N' Reel Resort in Chesapeake Beach is located along Maryland’s waterfront and is a perfect destination for day trips, weddings, family reunions, or an exciting adventure getaway. You can take advantage of year-round fun at this resort with marina water activities, casino game rooms and bingo games, luxurious trips to the rejuvenating spa, or entertaining concerts. You have the choice of staying in one of 72 rooms and suites on your weekend getaway , some of which feature limited views while others have complete waterfront views.

4165 Mears Avenue, Chesapeake Beach, Maryland 20732, 866-312-5596

Wylder Hotel, Tilghman Island - 1 hour 50 min

Since 1898 guests have been coming to Tilghman Island to relax and reconnect with nature at the original boarding house, which has now become the boutique Wylder Hotel.

Tilghman Island is a tiny 3-mile island in Chesapeake Bay where couples can spend their days relaxing around the salt-water pool, kayaking or paddle-boarding.

Other activities include cycling around the island, playing bocce ball or going on a fishing charter or romantic sunset cruise.

Tickler’s Crab Shack and Bar Mumbo offer craft cocktails, fabulous fresh fish and seafood dishes as well as other tasty meals for non-pescatarians.

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

Annapolis Waterfront Hotel

The Annapolis Waterfront Hotel is one of the Marriott Autograph Collection of luxury hotels, offering an excellent option for couples seeking a romantic getaway in Maryland.

Perched on the edge of the Annapolis Harbor, the hotel is perfectly positioned for sailing and other water sports.

It is also just steps from attractions like the Annapolis Historic Downtown and “The Yard”. All the rooms offer a serene cocoon where you can relax and unwind, surrounded by calming décor and brilliant views.

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

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

St. Michaels Harbour Inn, Marina & Spa, is located in the heart of Chesapeake Bay in St Michael’s, Maryland.

It is the perfect option for an overnight getaway or longer vacation stay; you will love spending time on the water, shopping, antiquing, or eating fresh fish during your stay.

St. Michaels Harbour Inn, Marina and Spa has three dining options available for guests. The Harbourside Grill, with its covered decks, warm fireplace, and unforgettable views, is a particular favorite, and it serves lunch, dinner, and cocktails. Complete your stay with a relaxing trip to the Spa at Harbour Inn and treat yourself to a body wrap, massage, or other indulging treatment.

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

The Reynolds Tavern - 35 minutes

Visiting the Reynolds Tavern in Annapolis, Maryland, a timeless luxurious Bed and Breakfast connected to one of the oldest taverns in the United States, is a wonderful vacation experience. Conveniently located in the heart of Church Circle, The Reynolds Tavern is mere steps from the State Capitol, and it is also quite close to the United States Naval Academy. You can feel the rich tradition and history of the establishment throughout your stay. The Reynolds Tavern features three refined two-room suites decorated with gorgeous antiques, exquisite oriental rugs, and soft, cozy bedding, all of which provide absolute comfort.

During your stay, you can enjoy lunch or dinner at the historic Reynolds Tavern, a restaurant with a rich ambience, amazing food, and a deep connection with history. You will not want to miss the classic experience of High Tea, which is served daily.

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

Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore

Located in Cambridge, Maryland, Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina is a 400-acre retreat overlooking the Choptank River that is perfect for a family getaway or a romantic escape. During your stay, you will have access to all the comforts and amenities a luxury Hyatt Resort typically provides. If you are hungry, you can choose from one of seven onsite restaurants. Tee-up at the championship 18-hole River Marsh Golf Club, practice your serve at the tennis courts, splash around the indoor and outdoor pools, and experience indulging pampering treatments at Sago Spa and Salon. If you are looking for romantic spa getaways in Maryland, this is relaxing vacation spot.

100 Heron Blvd. at Route 50, Cambridge, Maryland , 21613, 410-901-1234

We recommend this weekend itinerary if you decide to stay longer:

Wisp Resort

Wisp Resort is an amazing destination getaway for skiers, golfers, and outdoor enthusiasts. You can enjoy the western mountains of Maryland by skiing down 172 acres of slopes that receive over 100 inches of snow each season. Alternatively, you can enjoy a challenging mountainside game of golf at the beautiful 18-hole Lodestone Course.

During your stay, you have access to six dining options including the rustic lodge DC’s Bar & Restaurant, which serves breakfast, lunch, and dinner. If you are looking for year-round romantic Maryland resorts, Wisp Resort provides the perfect water, ski, golf, shopping, and adventure getaway for all your friends and family.

296 Marsh Hill Road, Mchenry, Maryland 21541, 301-859-3159

Gaylord National Resort

From the moment you check in to the Gaylord National Resort in National Harbor, MD, you will be in awe of your surroundings, and from the lobby atrium, you can see stunning views of the Potomac River and the nation’s capital.

One of the highlights of your stay will definitely include a visit to the 20,000 square fitness center featuring a pool, cardio equipment, and free weights. At Relache Spa, you can indulge in world-class treatments like wraps, massages, scrubs, or facials.

There are six fabulous onsite dining options. The Pose Rooftop with wrap around floor to ceiling windows overlooking Washington DC provides breathtaking and historical views you will not want to miss.

201 Waterfront Street, National Harbor, Maryland 20745, 301-965-4000

The Columbia Inn at Peralynna

Located in the rolling hills of Columbia, the historic Columbia Inn at Peralynna provides a luxurious, tranquil setting for romantic getaways, upscale business trips, corporate retreats, and intimate weddings. This unique, elegant boutique hotel captures the feel of a luxurious bed and breakfast.

During your stay, you can enjoy mingling with others by playing a game of pool, having a coffee in the atrium, or admiring the impressive four-story Great Room with games, movies, and books. The Columbia Inn at Peralynna offers 17 uniquely decorated room and grand suites. The Renaissance rooms are decorated with timeless antiques and replicas that will make you feel as though you have been transported to another era.

Your stay includes daily, delicious, made-to-order breakfasts with pastries you will crave long after you’ve returned home. Before leaving, be sure to enjoy wine, cheese, and crackers as you sit in the atrium from where you can take in spectacular views.

10605 State Route 108, Columbia, Maryland 21044, 410-715-4600

Great Oak Manor, Maryland

Located on Chesapeake Bay in Chestertown, Maryland, the Great Oak Manor is an 18th century country-style bed and breakfast. Experience a blend of relaxation and sophistication as you sit by the water watching the sunset and let your mind roam free at this historical estate.

Great Oak Manor has 12 inviting suites with elegant touches including plush towels, feather beds, and the finest bath amenities. Each morning you will wake up to a fresh homemade breakfast that you can savor while taking in the stunning bay views.

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

Sandaway Suites & Beach

Located just steps from the sand in Oxford, Maryland, Sandaway Suites & Beach blends the comfort of a hotel with world class service and the charm of a bed and breakfast. Sandaway Suites & Beach has convenient access to the beach as well as spectacular views, and the establishment provides a pampering experience that will delight you.

Spend some time on the warm sandy beach in a cozy chair, try kayaking, or take advantage of an in-room massage. When you are ready to unwind, head to the beach house, which is stocked with snacks and beverages. You can see amazing views of the bay and enjoy a light fresh breakfast while you savor your time away.

103 West Strand Road, Oxford, Maryland 21654, 888-726-3292

Lake Pointe Inn

Regardless of the season, the Lake Pointe Inn on the shores of Deep Creek Lake in McHenry promises to provide an unforgettable romantic getaway.

The luxury B&B offers 10 superbly appointed guestrooms, some of which overlook the lake while others offers views of the winter ski slopes.

All the rooms are lovely and would be great for a romantic retreat – check their website to choose your favorite. The surrounding area has much to offer in the way of attractions including antiquing, Amish Craft Trails, historic buildings, art galleries and more.

Lake Pointe Inn, 174 Lake Pointe Drive, McHenry, MD 21541, 301-804-6221

Laurel Grove Inn on the South River

Laurel Grove Inn on the South River has incredible river views and provides a peaceful and memorable getaway for every guest.

This inviting escape features a private dock on the South River and three acres of a large wooded area so guests can enjoy the great outdoors.

There are five uniquely decorated suites that will ensure your stay is comfortable and tranquil. You might want to consider staying in the River Hill Suite, which features a private entrance and separate living space with large windows providing spectacular views.

A plush couch is ideal for lounging and enjoying a relaxing afternoon.

2881 South Haven Rd, Annapolis, MD 21401, 443-370-2394

Gramercy Mansion, Maryland

Located close to Baltimore’s Inner Harbor in Stevenson, Maryland, Gramercy Mansion is an ideal location for anniversaries and weddings. This historical secluded mansion sits on 45 acres of exquisitely maintained gardens, including the Koinonia Organic Farm and a wildlife preserve.

Gramercy Mansion includes the Carriage House, which is open year round and displays timeless antiques and artwork.

1400 Greenspring Valley Road, Stevenson, MD 21153, 410-486-2405

Inn at Herrington Harbour - 1 hour 15 minutes

The Inn at Herrington Harbour in Chesapeake Bay, Maryland, is a perfect vacation place for water and boat lovers. With incredible views, 600 private boat slips, direct waterway access to the bay, and a 2-mile eco-trail this getaway is the perfect blend of relaxation and adventure. You can dine at Chesapeake Grille and Deli which features amazing views that will make your meal taste even better. You can also unwind by walking through the beautiful and peaceful gardens. If you are looking for romantic resorts in Maryland with a diverse choice of activities, this is a great place to visit.

7161 Lake Shore Drive, North Beach, Maryland 20714, 410-741-5100

Rocky Gap Casino and Resort

While staying at the Rocky Gap Casino Resort, you can appreciate beautiful panoramic views of the lush green mountains and nearby lake that will take your breath away. You can spend a pleasant evening in the casino, have an outdoor adventure, or treat yourself to a pampering treatment. Rocky Gap Casino and Resort is perfect for golf enthusiasts, who can enjoy a beautiful 18-hole course designed by Jack Nicklaus. Alternatively, you can spend time at the Spa at Rocky Gap and treat yourself to a wrap, facial, manicure, pedicure, or body treatment. The resort features five dining options including A Little Munch, which serves sandwiches, snacks, beer, and delightful baked goods.

16701 Lakeview Road, Flinstone, MD 21530, 301-784-8400

Haley Farm Spa and Retreat Center

From the moment you climb the steps to the wrap around deck with wood rocking chairs, you will settle in to a relaxing yet exciting experience at Haley Farm Inn and Retreat Center in Oakland, Maryland. The appeal of this 65-acre farm is the variety of activities in which you can partake, including sports adventures that are available year-round, pampering services at the delightful spa, or participate in meditation, yoga classes, and hiking. When staying at Haley Farm Spa and Retreat Center, guests can choose from four room types. Each of the buildings is warmly decorated and provides space for leisurely relaxation; the rooms include separate living areas, kitchens, and whirlpool tubs. Hayley’s Lakeside Cottage has three bedrooms and stairs that lead directly to your private dock. The cottages are perfect for a family or friend getaway.

16766 Garrett Highway, Oakland, MD 21550, 301-387-2471

Inn at Perry Cabin, St. Michaels

Perfectly positioned on the eastern shore of Maryland, just across the river from Chesapeake Bay, The Inn at Perry Cabin is a wonderful place to escape to for your next romantic getaway. Here, surrounded by the calming influence of the area you can your partner can look forward to doing as much or as little as you wish. The guestrooms and suites continue the relaxing theme with tranquil colors and all the luxuries you deserve. There is an on-site Links Golf Course where you can enjoy a challenging round of golf, or you can play tennis, go cycling or sample the water sports. The resort also boasts a wonderful outdoor swimming pool, a fitness room and, best of all, the Spa at Perry Cabin.

308 Watkins Lane, St. Michaels, MD 21663, 888-805-8885

Hotel Brexton

Hotel Brexton is a historic boutique hotel providing you with an intimate, first-class luxury vacation experience. Located in the culturally diverse Mt. Vernon area of Baltimore, the Queen Anne Style Hotel Brexton celebrates all walks of life.

Each morning, you will wake up to a delicious European Breakfast with delightful pastries. You will not want to miss enjoying a caffeinated beverage at the European Latte Lounge or snacking on wine and cheese, providing an opportunity to mingle and meet other guests at Hotel Brexton.

868 Park Avenue, Baltimore, MD 21201, 443-478-2100

1840s Carrollton Inn

The 1840s Carrollton Inn , located in the heart of Jonestown close to Little Italy and the Inner Harbour, gives you a traditional bed and breakfast experience you won’t soon forget. It features several connected row houses dating to the early 19th century that surround a beautiful and tranquil courtyard.

The 1840s Carrollton Inn is perfect for leisurely trips, business travels, or an intimate weekend. You will love starting your day with a fresh homemade breakfast served in the dining room or delivered to your room. The service is outstanding, and this bed and breakfast will continue to spoil you throughout your stay.

50 Albemarle Street, Baltimore, MD 21202, 410-385-1840

Savage River Lodge

Savage River Lodge is a lavish wooded retreat that is completely surrounded by the Savage River State Forest, which spans more than 700 acres throughout the Frostburg area. The 40-acre resort offers 18 miniature guest lodges for overnight stay, which have been handcrafted from white pine and are designed to coexist in harmony with their natural surroundings. Complimentary breakfast is delivered to each cabin and yurt each morning, with more than 13 miles of hiking trails available for visitors to explore the outdoors around them. A New American-style restaurant and bar is also offered, along with a ski shop, common-use library, and communal fire pit.

1600 Mt Aetna Rd, Frostburg, MD 21532, Phone: 301-689-3200

Live! Casino and Hotel, Hanover

Couples who enjoy the thrill of flirting with Lady Luck at the slots and tables will find that Live! Casino and Hotel offers an excellent weekend getaway destination. The hotel welcomes you to come and relax and unwind in one of 310 rooms and suites, all of which have been decorated with elegance and flair. Besides all the thrills of the casino, Live! presents wonderful live entertainment including boxing, music, comedy and much more.

Live! Casino and Hotel, 7002 Arundel Mills, Circle 7777, Hanover, MD 21076, 855-563-5483

The Inn at Chesapeake Bay Beach Club, Kent Island

A very popular venue for destination weddings, the The Inn at Chesapeake Bay Beach Club on Kent Island is also a perfect place to spend a romantic weekend getaway. The beautiful surroundings and the views over Chesapeake Bay encourage couples to relax and unwind – perhaps you can start your weekend by enjoying a pampering Couples Retreat at the on-site spa.The Inn has one of the original farm-to-fork eateries which showcase fresh farm produce (from their own gardens) and exceptional local fish and seafood.

The Inn at Chesapeake Bay Beach Club, 180 Pier One Road, Stevensville, MD 21666, 410 604 5900

The Lodges at Sunset Village, Mc Henry

The Lodges at Sunset Village on Deep Creek Lake have all the necessary requisites for a relaxing and romantic weekend getaway. You can choose which of the 6 types of log cabin lodges will best suit your needs – all have direct lake access, indoor fireplaces and large comfy beds (some also have hot tubs or whirlpool Baths). On-site activities for you to enjoy include walking, boating and paddling (rentals available), biking, horseback riding and birding.

The Lodges at Sunset Village, 23900 Garrett Highway, McHenry, MD 21541, 301-387-2227

Annapolis

Maryland’s capital Annapolis is nestled on the beautiful Chesapeake Bay and is often referred to as “The Sailing Capital of the World”. In addition to an abundance of covetable sail boats the city offers a great mix of history, restaurants and fun. You can explore the quaint brick streets of Annapolis on a Four Centuries Walking Tour or an Annapolis City Segway Tour or simply do a self-guided walking tour.