Vacation rentals in Scotland

Wits End Retreat-Relaxing Beautiful 3 Bedroom home

Leave your cares behind when you stay at Wits End. Relax with the whole family, take a couples getaway or stay long term at this peaceful property. This 1800 sq. ft. 3 bedroom 2 bathroom rancher style home has the comfort of modern amenities in a beautiful rural country-like setting. It's steps away from a community park, minutes away from several bodies of water including the Chesapeake Bay and a short drive to the Point Lookout State Park, St. Mary's College of MD and Patuxent Naval Air Base.

Family · Value · Laundry

Rodo Beach Cottage - Dog Friendly Private Beach wi

Free Wifi - Private Beach - Contactless Check-In - Pet Friendly - Tesla Charger - Linens, Soaps and Shampoo Provided. ****Summer weeks now booking only through ChesapeakeBayVacations (ig @ChesapeakeBayVacations)**** You'll feel like you're in your own world with the Chesapeake breeze as soon as you arrive at Rodo Beach Cottage. It's your very own beach front cottage to enjoy: * Crabbing off the pier * Biking around the Bay * Kayaks * Stand Up Paddle Boarding * Relaxing on the Hammock * P

Family · Location · Getting around

Water House at Scotland Beach

The Water House at Scotland Beach is a 4-bed, 3.5-bath vacation home in Scotland, Maryland. Nestled on 2 private acres and surrounded by water on three sides, it offers a serene escape for design lovers. Just an hour and forty-five minutes from DC, it’s very close yet extremely peaceful, private, and secluded. Enjoy crabbing, birdwatching, kayaking, swimming, and ultimate relaxation by the shore. This idyllic bayside retreat is perfect for gathering with loved ones, having fun, and recharging.

Family · Location · Bathroom

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Value · Location · Backyard

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Family · Value · Backyard

Secluded Waterfront:Kayaks, Sunrises & Unwind

This is a place you come when you need space: real space, quiet, and room to breathe. Set on 18 private acres along the Chesapeake Bay, our Ridge retreat offers a rare kind of calm: uninterrupted nature, open water views, and the feeling of being completely removed from noise, crowds, and schedules-- just land, water, sky, and time. Days unfold slowly with kayaking, crabbing, exploring the land. Evenings end by the fire under dark skies. This is not a tourist destination—it’s a true reset.

Location · Value · View

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

Family · Value · River

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

Location · Value · Grill

Pizza Friday

Magnificent 26-acre waterfront property just off the Potomac River. This secluded, quiet waterfront oasis boasts four-bedroom and two-full baths with large picture windows offering panoramic water views from almost every room. The large updated kitchen features stainless appliances, ample cabinetry, granite countertops, and a breakfast nook. There is a large sunny dock, a pizza oven, kayaks and a canoe to enjoy the water. If you're looking for the perfect weekend getaway, this is it!

Location · Family · Outdoor spaces

Waterfront Home w/ Private Dock, Beach & Fast WiFi

Private waterfront home on the Potomac River with a dock, private beach, kayaks, and excellent fishing access — perfect for families, remote work escapes, and anglers. Fish directly from the dock or walk 5 minutes to the marina for charter trips. Sleeps 6 comfortably with fast WiFi and peaceful sunrise views. Just 2 hours from DC, but it feels like a true reset with sunrise views directly over the water. Many guests return year after year for fishing season and summer family trips.

Value · Family · Nearby

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your newly renovated Lucas Cove Beach home awaits you with your own private sandy beach and pier with vast views of the water, new salt water hot tub steps away from the beach, four beautifully furnished bedrooms with Casper mattresses, an upstairs deck with Adirondack chairs to take in the water views and amazing sunrises while sipping a beverage or just relaxing, high speed Wi-Fi. Kayaks available for rent.

Family · Location · Condition

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

Location · Family · Parks