Free Dorsia 30-Day Trial
Exclusive Journey access: 30 days of free Dorsia reservations & events. Skip the line!
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
10 Guests
3 Bedrooms
2 Bathrooms
4.9 (59 Reviews)
Imagine waking up to the gentle lapping of the Chesapeake Bay, the morning sun casting glittering lights over the water, right outside your window. At Harbor View Haven, this is not just a dream but your everyday reality. Nestled in the historic town of Chestertown, this waterfront sanctuary is designed to offer an unparalleled blend of rustic charm and modern luxury, perfect for those seeking both relaxation and adventure.
As you step inside, the warmth of the natural light welcomes you, illuminating the finely crafted interiors that blend seamlessly with the outdoor vistas. The living area, with its plush seating and panoramic views, invites you to unwind as you gaze out at the serene waters. Each morning, brew a perfect cup of espresso with the state-of-the-art Jura machine, a ritual that energizes as much as it pleases the palate.
Outside, the expansive deck awaits. Here, you can soak in the hot tub under the open sky, feeling your cares melt away with each bubble. The outdoor gas fireplace offers a cozy retreat for chilly evenings, where you can wrap yourself in a soft blanket and enjoy the tranquil silence, punctuated only by the occasional call of distant seabirds. For those who crave activity, kayaks and bikes are readily available, inviting you to explore the picturesque surroundings at your own pace. Whether it’s a morning paddle in the calm waters or a leisurely bike ride through the leafy streets of Chestertown, each moment here enriches your stay.
Harbor View Haven also caters to those who delight in entertainment and social gatherings. Challenge your companions to a spirited game of ping-pong, or enjoy a sumptuous meal al fresco on the outdoor dining set, the fresh, salty air complementing your culinary creations.
As the day winds down, retreat to one of the elegantly appointed bedrooms, where the sound of the water seems to sing a lullaby. Here, in the embrace of fine linens and soft pillows, you’ll find peaceful slumber, dreaming of the adventures that await with the new dawn.
At Harbor View Haven, every detail is thoughtfully curated to ensure your stay is not just enjoyable, but truly unforgettable. It’s a place where each moment is a treasure, each breath a new opportunity to relax, recharge, and reconnect. Come and experience this magical waterfront retreat, where every visit feels like a return to a cherished home.
Imagine waking up to the gentle lapping of the Chesapeake Bay, the morning sun casting glittering lights over the water, right outside your window. At Harbor View Haven, this is not just a dream but your everyday reality. Nestled in the historic town of Chestertown, this waterfront sanctuary is designed to offer an unparalleled blend of rustic charm and modern luxury, perfect for those seeking both relaxation and adventure.
As you step inside, the warmth of the natural light welcomes you, illuminating the finely crafted interiors that blend seamlessly with the outdoor vistas. The living area, with its plush seating and panoramic views, invites you to unwind as you gaze out at the serene waters. Each morning, brew a perfect cup of espresso with the state-of-the-art Jura machine, a ritual that energizes as much as it pleases the palate.
Outside, the expansive deck awaits. Here, you can soak in the hot tub under the open sky, feeling your cares melt away with each bubble. The outdoor gas fireplace offers a cozy retreat for chilly evenings, where you can wrap yourself in a soft blanket and enjoy the tranquil silence, punctuated only by the occasional call of distant seabirds. For those who crave activity, kayaks and bikes are readily available, inviting you to explore the picturesque surroundings at your own pace. Whether it’s a morning paddle in the calm waters or a leisurely bike ride through the leafy streets of Chestertown, each moment here enriches your stay.
What we love about this stay
The hot tub is nice, but the real move is the deck at dawn—pull an espresso from the Jura, settle into one of the chairs facing the bay, and watch the light hit the Chesapeake before anyone else stirs. That first hour is the whole point. Afternoons, grab the kayaks and paddle east along the shoreline; the water is calmest before two o'clock and you'll spot herons if you're quiet about it. Save the outdoor fireplace for after dark—skip the blankets until the temperature actually drops, because the heat throws farther than you'd expect. If you're planning a group dinner, cook something simple and eat outside; the salty air does more for the food than any seasoning will. This place rewards you most when you slow down enough to notice the details.
Explore the residence
10 guests
2 Bathrooms
Member rates save up to 15% on every room
Free cancellation on most room types
Member rates save up to 15% on every room
Free cancellation on most room types
Browse the latest offers from Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Where you'll be staying
403 Fairview Dr., Chestertown, MD, 21620, US
Hear it from other travelers
Guest
MAR 2026
Looks smaller than pictures, but spotless clean and stylish interior and nicely furnished, more over stuffs for fun, kayak, bicycles, balls and hot tub! Wonderful view! <br/>If you want to cook, kitchen appliances are little bit old, which is really minor. Landon is quick to respond and takes care of things very well.<br/>It was one of the best memory of family vacation!
Guest
MAR 2026
Upon arrival at this very special spot my friends and I felt instantly at ease. The home is immaculate and well situated. It is cozy and inviting. The atmosphere is calming, inside and out. There are plenty of options for an ultimate lounging experience! Living room downstairs, sweet hangout area upstairs, upper deck with a super comfy set up that is perfect for watching the Mama Osprey in her nest! Outdoor patio seating, adirondack chairs by the fire pit and … our favorite place of all to lounge was the hot tub!! Gazing at the stars while the fireflies were twinkling was incredible! We kayaked, and floated around on the inner tubes and had so much fun playing ping pong. The sunsets were phenomenal! This Airbnb was all that we hoped it would be and more! Watching the Osprey in her nest with her babies was a highlight for us. Landon is a fantastic host and this house is top notch!! Chestertown has some cute shops and a great bookstore and we loved Modern Stone Age Kitchen for breakfast!
Guest
MAR 2026
Great place to stay, cannot recommend it enough!
Guest
MAR 2026
My family had a great time! Chestertown is a cute town. We enjoyed going to the bookstore, checking out the local restaurants and the beautiful scenery. The house was comfortable, family friendly and a spot we would love to check out again when the weather gets warmer :)
Guest
MAR 2026
We had a wonderful weekend at this property. The beautiful waterfront views make the property the perfect place to unwind and have a relaxing vacation. There’s also a generous amount of outdoor seating to soak up the sun and take in the beautiful views. The property has everything you need for your stay, all you need to do is load up the refrigerator with groceries. There’s a BBQ grill, all the utensils you need and seasonings for cooking. I look forward to visiting more of Landon’s properties as he and his team are very hospitable and have done a great job hosting.
Watch this Stay
Get notified when this stay runs special offers or becomes available during your preferred travel dates. We'll also connect you to the property so you can be eligible for insider rewards and premium experiences.
Similar stays around Chestertown
Follow Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Follow our social media to gain instant access to all things Harbor View Haven | Waterfront w/ HOT TUB + Dock!: discounts, photos, updates and giveaways!