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05-December-2025 Plan Your Stay
Winter at Chesapeake Paradise has quietly become one of the most breathtaking, soul-soothing experiences on the Chesapeake Bay. Many of our guests who stay during the colder months actually prefer it to summer — and the honeymooners who checked out this morning said it best:
“It was magnificent.”
If you’ve ever longed for a peaceful waterfront retreat where the pace slows down, the sunsets glow deeper, and the prices drop dramatically, winter at Chesapeake Paradise is the perfect escape.
Unlike harsh northern winters, the Chesapeake Bay offers a bright, mild season filled with cozy indoor fires, sparkling water views, fiery winter sunsets, and a surprising abundance of tundra swans and waterfowl. Guests often tell us their winter stay gave them a boost in mood, a deeper connection to nature, and a sense of calm they didn’t realize they were missing.
After 16 years of hosting thousands of delighted guests, Chesapeake Paradise has officially stepped into a new era of beauty. Nearly all of our spaces have been remodeled — bright, spacious, tasteful, and designed for comfort.
Here’s a peek at where you can stay this winter:
The crown jewel of the property. Spacious, bright, and sparkling after its recent remodel. Perfect for families, groups, or anyone craving expansive beauty on the water.
Our honeymooners adored it and for good reason. Wake up wrapped in golden sunrise, with luxury finishes throughout.
The entire downstairs of the main house plus the brand-new foyer, morning room, porch, and luxurious Sunrise Suite upstairs. Cozy, private, and a guest favorite.
If you love natural light, this is your dream. A bright solarium bedroom with balcony and windows everywhere, bringing the Bay right to your bedside.
Warm, roomy, and beloved by families and pets alike. Perfect for long or short-term stays, complete with a fireplace for extra winter coziness.
Need more space? Add the Carriage House and enjoy the perfect two-building combo for retreats, families, or group gatherings.
There’s no inflation here — winter is actually when we lower our prices dramatically. Guests routinely tell us they can’t believe what they get for the price, especially compared to Airbnb and VRBO.
Here’s why winter is the best time to book:
No booking fees on our brand-new website
$100 coupon available on the site
15 percent off stays through April 1 for returning guests
10 percent more off for mailing list members
$50 off for each friend you refer who completes a stay
Huge discounts for long-term winter stays (1–6 months)
Winter is the season for romantic getaways, solo resets, finishing big projects, remote working, reflective retreats, and family bonding. Chesapeake Paradise naturally encourages you to slow down, smile more, reconnect, play, and restore your energy.
Whether you’re curling up by the fire, listening to the water, watching the birds, or walking the peaceful shoreline, your winter stay will stay with you long after you leave.
Great news. We currently have this weekend available, and we are waiving the three-night minimum for winter guests. Several upcoming winter weeks are also open.
If you or someone you know needs sanctuary, productivity, or simply a beautiful place to breathe, this is the perfect time to come.
Remember that longer stays come with big discounts.
Need a winter home for your boat or trailer? We have two beautiful boat slips and two acres of space for trailering. Email us your dates and boat details to learn more.
Winter is one of the most spacious, magical, and affordable times to visit. And when you book directly, you save significantly.
Browse openings and book fee-free at:
ChesapeakeParadise.com
Or contact Shawn directly:
+1 (301) 785-0545
You can also reply to this email anytime.
We can’t wait to welcome you to your cozy winter sanctuary on the water.
Happy Holidays from Chesapeake Paradise!