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Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

Long Beach Wellness Retreat Hot tub/Sauna/Plunge

Long Beach Wellness Retreat | A Romantic Chesapeake Bay Escape 🌊Waterfront w/ beach 🛶Kayaks- paddleboard ☕️Espresso machine 🌹Romantic 🧖‍♀️Sauna,hot tub and cold plunge Welcome to Long Beach Wellness Retreat, our cozy coastal cottage designed for couples seeking a peaceful place to unwind, reconnect, and reset. Nestled along a sandy stretch of the upper Chesapeake Bay, this newly renovated waterfront retreat blends wellness, relaxation, and coastal charm into one unforgettable getaway.

Swan Lake

Swan Lake is located in Southern Lancaster County. The house is situated on 12.5 Acres with a pond and gazebo. This is a secluded family destination in Amish country but close to numerous amenities. You will enjoy beautiful views of the pond from all floors and decks. Numerous hiking trails and the Susquehanna River are within minutes. Working Amish farms surround this property and yet you are within 30 Minutes of Lancaster City. PLEASE NOTE WE REQUIRE RENTERS TO BE A MIN Of 25 YRS OLD

Breathtaking Waterfront w/pool and private dock

Only 1 week left for Summer 2026! Fall dates still available. This incredible 4-bed 2-bath water-facing home is the ultimate getaway. Pool/Spa are Seasonal **open mid May through Sept only** Pool and hot tub are **closed Oct - May** We do not have a separate stand alone hot tub. Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with a $125 docking fee) Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2)

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

East Baker Bungalow

Welcome to our home away from home on Bush River! Relax and unwind overlooking the beautiful water where you can bring your own boat. Whether you're here for the weekend to escape the hustle and bustle or bringing all your family and friends for a week on the water, we have something for everyone! Bring your own Boat, kayak or even fishing off your own private pier. Only 40 minutes from Baltimore's airport, 15 minutes to Ripken Stadium and super close to shops and grocery stores!

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

Waterfront Farmhouse Retreat w/ Hot Tub & Fire Pit

Tucked along the banks of the Cohansey River, The Foxtail is a design-forward waterfront retreat set at the end of a long private lane. Recently refreshed throughout, the home blends its 1860s character with thoughtful modern updates, including a brand new kitchen, all new operable windows with screens, updated baths, and custom window treatments throughout. The result is a peaceful, comfortable river house that feels considered without feeling precious.

Beachfront Sunsets on the Water at Oakwood Beach

You’ll instantly relax when you arrive at this private beachfront home on the beautiful Delaware River (2020 River of the year!). This hidden gem is off the beaten path, making it perfect for you to escape the hustle and bustle of your busy day-to-day. You’ll love the amazing sunsets and water fun — walk out the back door directly onto the large deck and sandy beach. Message us for information about the local wineries and distilleries or for kayaking!

Farm House w/ Water Access (near Chestertown)

The perfect setting for family and friends (up to eight people) to gather and get away to relax. Situated on 140 acres adjacent to Still Pond Creek in Worton, there's room for everyone to spread out -- enjoy the fresh air, outdoor activities and relax in solitude watching abundant wildlife (birds, deer, rabbits, groundhogs, and more!). Chestertown is just 8 miles away with a year round farmer's market, local shopping, art galleries and more.

Catching Sunsets on the Bay

Come and enjoy this brand new home, built for making memories on the Chesapeake Bay! Our spacious 3 bedroom, 2.5 bath is perfect for your next getaway. Our cozy, yet modern home is within feet of the Northeast River where you can take in the beautiful views, go kayaking, swimming or boating, or take a 12 minute drive to the new Great Wolf Lodge! Our home is perfect for couples or families as we have games, toys, and a pack n play if needed!

Chesapeake Bay Cottage

This cozy home, just a block away from the Chesapeake Bay, offers the perfect mix of comfort, convenience, and outdoor charm. Tucked into a small, walkable neighborhood, the location is ideal for anyone looking to spend time near the water. Whether you’re planning a fishing weekend, a peaceful solo escape, or an exciting holiday with friends, this space offers the flexibility and ease that make everything feel effortless.