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Chesapeake Point | Waterfront w/ HOT TUB + Beach!
20 Guests
7 Bedrooms
4 Bathrooms
4.9 (18 Reviews)
Imagine a retreat where the horizon is an endless expanse of sparkling waters and the mornings are heralded by the soft sounds of the Chesapeake Bay lapping against its shores. Welcome to Chesapeake Point, a grand colonial oasis where luxury and tranquility meet amidst the natural beauty of Elkton, Maryland.
As you step through the doors of this 7,000 square foot masterpiece, you're greeted by a flood of natural light from expansive windows framing the bay's mesmerizing vistas. Each room is a testament to refined taste, adorned with sophisticated decor that complements the home's modern colonial architecture. The seamless blend of elegant furnishings and contemporary amenities creates an environment that is both grand and inviting.
Chesapeake Point is designed for those who seek a unique connection with nature without sacrificing comfort. Start your day with a serene kayak ride from your private dock, navigating the calm waters as the sun rises, painting the sky in hues of gold and amber. Return to indulge in a leisurely breakfast on the terrace, where the only interruption is the gentle call of seabirds.
Your afternoons are for relaxation. Picture yourself in the outdoor hot tub, soaking in warm bubbles while gazing out at the vast bay, or perhaps curled up with a book in one of the three plush living rooms, each offering a distinct view and ambiance. As evening falls, gather your loved ones around the fire pit, sharing stories and laughter under a canopy of stars, the air filled with the comforting scent of the grill.
Fitness enthusiasts will appreciate the full home gym, equipped with everything needed to maintain your fitness regime, followed by a refreshing dip in the bay or a casual game in the gaming areas. Every corner of Chesapeake Point is thoughtfully designed to enhance your stay, ensuring that each moment is filled with enjoyment and relaxation.
As night descends, the bay becomes a mirror, reflecting the moon's silvery glow. It's the perfect backdrop for a night of peaceful sleep in one of the luxuriously appointed bedrooms, each a sanctuary of comfort ensuring you wake up refreshed, ready to do it all over again.
Chesapeake Point isn't just a place to stay; it's a journey into a waterfront lifestyle where every detail is curated for discerning guests who aspire for nothing less than extraordinary. Here, each day is a chapter in a story of unforgettable luxury, written by the rhythmic ebb and flow of the Chesapeake Bay.
Embrace the elegance, live the serenity, and make memories that will last a lifetime at Chesapeake Point.
Imagine a retreat where the horizon is an endless expanse of sparkling waters and the mornings are heralded by the soft sounds of the Chesapeake Bay lapping against its shores. Welcome to Chesapeake Point, a grand colonial oasis where luxury and tranquility meet amidst the natural beauty of Elkton, Maryland.
As you step through the doors of this 7,000 square foot masterpiece, you're greeted by a flood of natural light from expansive windows framing the bay's mesmerizing vistas. Each room is a testament to refined taste, adorned with sophisticated decor that complements the home's modern colonial architecture. The seamless blend of elegant furnishings and contemporary amenities creates an environment that is both grand and inviting.
Chesapeake Point is designed for those who seek a unique connection with nature without sacrificing comfort. Start your day with a serene kayak ride from your private dock, navigating the calm waters as the sun rises, painting the sky in hues of gold and amber. Return to indulge in a leisurely breakfast on the terrace, where the only interruption is the gentle call of seabirds.
What we love about this stay
Get on the water before breakfast — launch a kayak from the private dock right at sunrise when the Chesapeake is glassy and the light turns everything amber. It's the single best moment here, and it sets the tone for the entire stay. Mornings after, take your coffee on the terrace rather than inside; the seabird activity alone is worth the early chill. In the evenings, skip retreating to the living rooms and commit to the fire pit — the bay becomes a mirror after dark, and the stillness out there is genuinely disarming. One practical note: bring layers. The water cools the air faster than you'd expect, even in summer. This place rewards you most when you slow down and let the tides dictate the rhythm.
Explore the residence
20 guests
4 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 Chesapeake Point | Waterfront w/ HOT TUB + Beach!
Where you'll be staying
1036 Oldfield Point Rd., Elkton, MD, 21921, US
Hear it from other travelers
Guest
MAR 2026
Fantastic house in an off-the-grid location, ideal for large groups wanting to unwind and enjoy beautiful views, water sports, bon fires, with plenty of space to hang out, unwind and connect. This house provided us with a location to come together, catch up, share laughs and make a few more wonderful memories with enough space for quiet downtime, a workout, or space to play games and laugh loudly without fear of disrupting others. The wifi isn't the best, but that was of little concern to most of us. Highly recommend.
Guest
MAR 2026
Beautiful property and very well stocked with supplies. The private beach is on a bay with very calm water - perfect for young kids. Would love to come back when it’s warmer! Wifi wasn’t the fastest and the signal wasn’t great at the far end of the house, so just be prepared for that.
Guest
SEP 2023
Stayed in a lot of rented locations around the US and Europe and this was the best home and location I've stayed in. The home is better than the pictures and, if you cannot relax here, you won't be able to relax anywhere. We had a birthday celebration for some 80+ year olds and it was a great time.<br/>Highlights:<br/>- Secluded and quiet. <br/>- Wonderful, unobstructed water views.<br/>- Tree spacing in the yard, which I don't usually pay attention to, really helped compliment the house and backyard.<br/>- Yard was much bigger than the pictures made it seem.<br/>- Spacing inside the house was great so that our family and friends were not on top of each other. <br/>- Bedrooms are quiet and couches were comfortable.<br/>- We did not try the outdoor hot tub, but it looked inviting.<br/>- Lots of amenities and supplies.<br/>Host<br/>- Communicative and professional.<br/>- We had storms go through one night during our stay and lost power. The host made things right for us. Thank you again.<br/>What a house!
Guest
OCT 2023
I had a group of families stay for an event. Landon was very quick with communication. Place as described in the pictures. I would definitely recommend it for family gatherings.
Guest
MAR 2026
We thoroughly enjoyed spending six nights in this spotless and comfortable house with gorgeous views of the river. This is an excellent place for large family gatherings, with a hot tub and fire pit outside, and a fabulous game room and work out space for fun and exercise, rain or shine. The surrounding countryside is lovely, and farm stands and fresh seafood are readily available. Landon is an outstanding host who answered all our questions promptly and graciously. We will definitely be back next year!
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