Romantic Hotels for a Couple's Getaway in Chestertown (Maryland)

Brampton Bed and Breakfast Inn

Chestertown - Montana

At the Brampton Inn, you'll be surrounded by 19th century elegance and modern amenities. Enjoy a peaceful stay in an Emory Suite, with luxurious linens, an individual HVAC, and complimentary refreshments. Relax on the wrap-around terrace with ceiling fans or in one of the well appointed common rooms while taking in the lush gardens and outdoor seating. Delight in a charcuterie tray and cheese boards, wine and chocolate pairings, and delicious baked goods available round the clock. Our friendly staff, including the charming French hostess, will make sure your stay is comfortable and carefree. Come visit the Brampton Inn and experience Maryland's Eastern Shore in style!

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More Romantic Hotels for a Couple's Getaway near Chestertown

Inn at Haven Harbour

Rock Hall - Montana

10 miles from Chestertown

The Inn at Haven Harbour is a stunning, one-of-a-kind property located on the beautiful Eastern Shore of Maryland. Relax and enjoy the unique accommodations, full marina, on-site pool and fitness center, private beach and fire pit, and a variety of outdoor activities including biking, swimming, and water sports. Guests can also take advantage of the onsite bar and shared lounge. The Inn is located near Chestertown and is the perfect spot for a weekend getaway or a longer stay. Be sure to check out the annual Oyster Festival in nearby Rock Hall. With its attentive staff, clean rooms, and great food, an unforgettable experience awaits you at the Inn at Haven Harbour.

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Inn at Osprey Point

Rock Hall - Montana

10 miles from Chestertown

Inn at Osprey Point is a beautiful and cozy retreat in Rock Hall, offering spectacular views of the water, tasteful furnishings, and a delightful breakfast buffet. Enjoy the outdoor pool and restaurant, kayaks and canoes, and a friendly, helpful staff. Revel in the pastoral farms and cottages along the Swan River, and be sure to enjoy the homemade cookies in your room. Our host Terry is warm and hospitable, ensuring your every need is met. Be sure to visit the charming port where you can take a walk in the piers. Come experience the comfort and beauty of Inn at Osprey Point!

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Haven Point Inn

Rock Hall - Montana

10 miles from Chestertown

Haven Point Inn in Rock Hall is a perfect place for a peaceful and welcoming getaway. Hosts Judith and Paul are the perfect ambassadors for the area - they provided us with helpful tips and advice on the best places to visit, as well as making our stay as comfortable as possible. The inn has comfortable rooms and a large garden to explore, complete with stunning roses in bloom. The inn also offers free wifi and a paid airport shuttle service. Breakfast is served daily and is delicious, and the coffee is available in a nearby room. Bicycles are available for use, making it easy to explore the nearby attractions, including the Fisherman's Wharf and Eastern Shores Nature Reserve. All in all, it's a great place to relax and take in all the beauty that Rock Hall has to offer.

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Inn at Huntingfield Creek

Rock Hall - Montana

10 miles from Chestertown

The Inn at Huntingfield Creek is a tranquil and picturesque retreat, surrounded by beautiful grounds, a soy bean farm, a pine tree forest, a pond and a stunning view of Chesapeake Bay. Enjoy a peaceful stay in one of our comfortable air-conditioned rooms or cottages, complete with Wi-Fi, a coffee maker and all the supplies you need. Our friendly and attentive owners will ensure you feel welcomed and relaxed. Enjoy breakfast at the inn's family-style restaurant or use vouchers for the Jazz Rock cafe in Rock Hall. Plus, you can explore the area with our helpful golf cart. Come experience the perfect escape and reconnect with your special someone at the Inn at Huntingfield Creek.

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The Inn at Chesapeake Bay Beach Club

Stevensville - Montana

21 miles from Chestertown

The Inn at Chesapeake Bay Beach Club is a luxurious and inviting getaway, perfect for a restful retreat. Boasting a seasonal outdoor pool, fitness centre, private parking, garden, restaurant and shared lounge, as well as free WiFi, this hotel is sure to make you feel right at home. Guests can enjoy a king suite with two separate rooms, one with a fireplace, plus there are rocking chairs around a fire pit. There's also two pools, plus the town is charming and friendly. The hotel is well-maintained, rooms are great and meals are delicious, with excellent hospitality and great safety measures put in place. With a relaxing and private atmosphere, the Inn at Chesapeake Bay Beach Club is the perfect spot for a serene getaway.

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Vandiver Inn

Havre de Grace - Montana

23 miles from Chestertown

The Vandiver Inn in Havre de Grace is a charming, historic inn that offers luxurious 3-star accommodations, a shared lounge and bar, and a beautiful garden. Our stay was comfortable and enjoyable, with air-conditioned rooms and private bathrooms, as well as beds that were incredibly comfortable. Safety was assured in the lovely neighborhood and the staff was friendly and helpful. Breakfast was fantastic and the chef cooked in front of us, making us feel welcome. The added bonus of a community park and marina overlook was great, and the evening was perfect, sipping wine on the wide porch under the moonlight. We had dinner at the supper club, and enjoyed the complimentary waffles and eggs for breakfast the next day. The Chef was a real treat! We would definitely recommend staying at the Vandiver Inn.

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Flag House Inn

Annapolis - Montana

27 miles from Chestertown

Flag House Inn is an outstanding 5-star accommodation located in the heart of Annapolis. Enjoy air-conditioned rooms with private bathrooms and free WiFi, plus a shared lounge and a breakfast made with love. The hosts are incredibly friendly and welcoming, providing personalized insight and tips for exploring the area. The location is unbeatable, just a hundred yards away from the center of town and across the street from the Naval Academy. Proximity to local attractions such as Carroll Park and Sports Legends Museum at Camden Yards is also great. Enjoy a unique experience with a luxurious breakfast and a relaxing swing on the porch. With free parking and excellent amenities, Flag House Inn is the perfect place to spend your holidays.

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134 Prince - Luxury Boutique Hotel

Annapolis - Montana

27 miles from Chestertown

Welcome to 134 Prince – Luxury Boutique Hotel in the heart of beautiful Annapolis. Our 170+ year old house has been lovingly restored to provide 5-star accommodation. Our charming Regatta Suite is situated on the top floor of the house with a gorgeous marble shower and plush, soft towels. Enjoy complimentary use of the Nespresso machine in the front parlor, as well as a selection of whiskey and port. You'll be greeted by our friendly and welcoming staff, who will go above and beyond to ensure a pleasant stay. Enjoy a hot, custom-made breakfast by Miguel in the cozy kitchen and take advantage of the convenient location, just one block away from the harbor, restaurants and shopping. Relax in the comfort of our immaculate and stylish rooms and be sure to take advantage of the civilized happy hour events. We look forward to seeing you soon at 134 Prince – Luxury Boutique Hotel!

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Graduate Annapolis

Annapolis - Montana

27 miles from Chestertown

This downtown Annapolis hotel offers modern comfort, convenience and style. Featuring a contemporary restaurant, free WiFi in all guest rooms, and just 1.6 km from the United States Naval Academy and Navy-Marine Corps Memorial Stadium, this hotel is perfect for your stay in Annapolis. Enjoy the well-equipped rooms with TV, refrigerator, desk, safe, and blowdryer, as well as plenty of electrical plugs and USB ports. The hotel's bar/restaurant is open late and serves a variety of snacks and meals. Plus, the room's view of the ballroom is stunning. Enjoy a walk to Main St. and explore the shops, restaurants, and nearby US Naval Academy and St. John's College. With easy access to parking in the basement, you can't go wrong with this centrally located Annapolis hotel.

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Four Seasons Baltimore

Baltimore - Montana

28 miles from Chestertown

This 5-star luxury hotel located in Baltimore’s Inner Harbor offers a wonderful and unique experience, with free Wi-Fi, full service spa, rooftop infinity pool, and four on-site dining facilities. The National Aquarium is just a kilometer away. Enjoy the plush linens, cozy robes and delicious room service. Relax in the deep bathtub or on the harbor view balcony before you take in the breathtaking views from the rooftop bar, The Bygone. Enjoy a variety of dining experiences, from Maximon's Mexican restaurant to classic oyster bar. The helpful and polite staff will ensure your stay is perfect, while the location provides easy access to shopping, bars and restaurants. Despite the COVID closures, the hotel still provides a luxurious and safe experience. The room temperature may be cold at times, but the overall experience will be unforgettable.

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BlancNoir

Baltimore - Montana

28 miles from Chestertown

BlancNoir is the perfect Bed & Breakfast for anyone looking for a cozy getaway. Located in the heart of Little Italy, Baltimore, it offers guests a relaxing stay in a homey atmosphere. Each room is equipped with a private bathroom, free WiFi access, and a flat-screen cable TV. The hosts, Bill and Tonia, make sure each guest feels welcome and taken care of. Breakfast is made-from-scratch and is sure to hit the spot. Take a stroll around the area and explore the restaurants and shops within walking distance. Whether you’re here for a romantic getaway or a family vacation, you’re sure to have a memorable stay at BlancNoir.

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