Vacation rentals in Sassafras River

The Mint Cottage in Chesapeake City

The Mint Cottage is new to the air bnb market. It is a 3 bedroom Cape Cod on .5 acre lot in Charming Chesapeake City! The 1st floor features a master bedroom suite with updated amenities, large living room and kitchen, PLUS a full hair and makeup station (great for bridal parties). The 2nd floor has two bedrooms- a queen and 2 twin beds. The house features 3 full baths.The back yard has a private swimming pool, fire pit and patio. Terrific location to walk to waterfront, shops, and restaurants!

The Roundtop Chalet (romantic couples retreat)

Indulge in a getaway to our charming cabin, the perfect retreat for all your special celebrations - be it anniversaries, birthdays, or simply a much-needed escape from routine. Perfectly designed for romantic getaways, this cabin seamlessly blends rustic charm with modern comforts. Savour the warmth of a cozy fireplace, unwinding in a hot tub,and indulge with unlimited lattes, crafted by our Breville Touch Espresso Machine. Embrace serenity at its finest and make memories that will last forever

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures. *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Sugar Shack| A-Frame Tiny Home w/ Hot Tub

Kick back and relax in this calm, stylish space. The Sugar Shack is a modern tiny home is located on top of a mountain and has spectacular mountain views. Sit on the wrap around porch with your loved one or relax in the hot tub right outside the door and enjoy watching the wildlife. The interior has a modern design and you will experience a cozy and romantic atmosphere the moment you walk in. It truly is a perfect spot to unwind and reconnect with yourself, your loved one, and nature!

Spectacular views, intimate dome

Come experience a truly one of a kind polycarbonate dome tucked away in the Appalachian mountains! Situated on the mountainside overlooking the scenic Cumberland valley. Complete privacy, stunning sunsets, and amazing amenities! The dome is climate controlled. The spacious deck is equipped with a meticulously maintained hot tub, and a blackstone griddle. This offers the unique opportunity to be immersed in nature, yet enjoy numerous amenities and comfort.

Cozy Cottage •HOT TUB • FIRE PIT• Peaceful Getaway

🌾 Welcome to Your Cozy Farm Retreat A peaceful, private guest cottage located on our small, quiet farm — complete with your own private hot tub, fire pit, and beautiful views. This is the perfect escape to relax, recharge, and enjoy the countryside. Sip coffee overlooking the fields, unwind in the hot tub under the stars, or explore the local farms, breweries, and trails nearby. Perfect for couples or solo travelers seeking a quiet getaway.

Blue Heron Farm Waterfront Chalet

Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.

Bohemia Bungalow

Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.

The Hepburn-Hot Tub & Fire Pit

The Hepburn is a beautifully renovated and decorated by home by Harlow Grey Homes. This meticulously restored glass cabin is located on over an acre of private grounds on a serene 75 acre lake. Firewood included! The separate seven-person hot tub is OPEN for the season. The private pool + built-in spa is closed and is set to reopen mid May 2025

*Woodland Chalet* Hot Tub - Fire Pit - Grill

Welcome to your cozy woodland retreat! Nestled in a serene forest, this charming one-bedroom Airbnb offers a perfect blend of style and tranquility. Designed with a modern aesthetic, the space features chic furnishings, warm modern accents, and large windows that invite natural light and breathtaking views of the surrounding trees.