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This Stevensville, Maryland waterfront home, located in Queen Anne's County, offers easy access to the Cross Island Trail, Blue Heron Golf Course, and Mowbray Park (3-5 minute drive).
The 1370-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps seven guests, and includes a private pool (open May 15-October 15), four kayaks, crabbing gear, and a renovated kitchen with granite countertops and stainless steel appliances.

This 5-bedroom vacation rental is located on Maryland's Eastern Shore, just a short drive from the charming town of Easton. The property is situated in a peaceful, rural setting, offering a tranquil escape from the hustle and bustle of city life.
This spacious home features a large, open floor plan perfect for entertaining, with enough room to comfortably accommodate up to 10 guests. The well-equipped kitchen, complete with a dishwasher, microwave, and refrigerator, is ideal for preparing meals, and the property also includes a swimming pool, parking, and internet access.

This Stevensville house, located in Paradise Island, offers convenient access to Annapolis Harbor (23 miles), Sandy Point State Park (14 miles), and the U.S. Naval Academy (21 miles).
The 1,370-square-foot property features one bedroom, accommodates up to 13 guests, includes a private pool, free Wi-Fi, and free parking, and provides a fully equipped kitchen.

This spacious vacation home is located in Trappe, just a short drive from the Academy of the Arts and a scenic trip to Federalsburg Marina. The house offers a comfortable stay for large groups or families, with four bedrooms, three bathrooms, and a generous floor area of 2200 square feet. Enjoy the private pool, the shaded gazebo, and the fully equipped kitchen with a dishwasher and oven. Relax in the air-conditioned house with free Wi-Fi access and a flat-screen TV.

Shipwright Cottage is located just eight miles from the charming town of St. Michaels, Maryland, offering a peaceful escape from the hustle and bustle of city life. The cottage consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The two-bedroom cottage comfortably sleeps four guests and spans 1,190 square feet. Shipwright Cottage provides a fully equipped kitchen, a screened porch, a spa, and access to kayaks, bicycles, and a bike trailer, allowing guests to enjoy both indoor and outdoor activities.

This Stevensville, Maryland island retreat offers a 3-bedroom, 2-bathroom home, sleeping up to 8 guests, and is conveniently located near various wedding venues and restaurants, with easy access to the Bay Bridge for Annapolis and Washington, D.C. excursions.
The 2023-renovated property features a large kitchen island, spacious back deck with a fire pit, and a modern island-themed interior, including air conditioning, a garden, parking, and internet access; pets are welcome.

This waterfront estate on the Eastern Bay of the Chesapeake Bay in McDaniel is approximately 10 miles from St. Michaels and 22 miles from Easton, offering expansive 12+ acre grounds with Chesapeake Bay views. This 6-bedroom, 6-bathroom residence accommodates up to 12 guests and features a private dock with water and electricity, a heated saltwater pool, a year-round hot tub, and a gourmet kitchen.

This waterfront apartment is conveniently located just over the bridge entering St. Michaels, a minute from the town itself, 7 minutes from Easton, and 30 seconds from The Oaks Wedding Resort. Rated as excellent by previous guests, it has two large bedrooms and two full bathrooms, with a guest capacity of 4.
The apartment offers a deck for entertaining, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, a garden, and parking. Local shops and restaurants are within minutes of the house, and outdoor activities such as fishing, kayaking, paddle boarding, biking, and hiking are also available nearby.

This vacation home is situated in Stevensville, offering water views and an idyllic garden setting on Kent Island, 22 miles from Annapolis Harbor and 32 miles from Baltimore - Washington International Airport.
This spacious 1490 square foot house accommodates up to 21 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, complimentary private parking, free Wi-Fi, air conditioning, and an outdoor patio for relaxation.

This charming apartment in St. Michaels is just steps from the Auto Museum, Maritime Museum, YMCA, and a variety of restaurants. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom apartment is ideal for two guests.
The 480-square-foot apartment features a kitchen with a fridge, freezer, and microwave, as well as air conditioning, a Jacuzzi, a terrace or balcony, a garden, and parking. Laundry facilities are available upon request for longer-term renters.

This Stevensville beach house is located just 9 miles from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park, offering easy access to local attractions. The property has excellent ratings for user experience, location, and cleanliness.
This 1800 square foot vacation rental comfortably sleeps 14 guests in its four bedrooms. The house features a fully equipped kitchen, a fireplace, a jetted tub, a private terrace, a garden, a spa, a tennis court, and a playground, perfect for relaxing and entertaining.

This pet-friendly cottage on Tilghman Island offers 3 bedrooms and 2 bathrooms for up to 6 guests, located in a rural area with easy access to marinas, waterfront dining, and within 2 miles of the Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum.
Enjoy a screened porch with dining for six, a fully stocked kitchen, keyless entry, and nearby opportunities for fishing, boating, and cycling.

This waterfront home sits on a 3-acre property near St. Michaels and Easton, a nationally-recognized town. Guests rave about its excellent location, cleanliness, and overall experience.
This charming apartment sleeps 6 guests and features a fully equipped kitchen, a cozy living room with a fireplace, and a large deck with a screened porch. Guests can enjoy kayaking, biking, and grilling, plus the property includes a fire pit, yard games, and a private pier with a tidal cove.

This Bristol B 40 Yawl accommodation is located in a protected marina on a lagoon near Stevensville, offering lagoon and nature views with direct access to sunrises and sunsets. This boat sleeps up to 3 guests and features 1 bedroom, 1 bathroom, internet, a kitchen, and parking, providing a unique waterside experience with interior teak and mahogany woodwork.

This Oxford apartment rental is conveniently located a 14-minute walk from the Oxford Museum and a 15-minute drive from the Talbot County Visitor Center.
The three-bedroom, two-bathroom vacation home features a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, free Wi-Fi, parking, and proximity to attractions like the Academy Art Museum.

This Tilghman Island rental is conveniently located on the island, offering waterfront views and easy access to local restaurants and shops.
This 1470-square-foot, three-bedroom, two-bathroom house sleeps six, features a well-equipped kitchen with a dishwasher and microwave, and includes linens, towels, and a starter supply pack.