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01-November-2026 Plan Your Stay
A winter waterfront getaway in Maryland with wide-open water views, migrating swans and geese, fireplaces, a hot tub, and five different ways to stay near Annapolis
Most people picture Chesapeake Paradise in summer: kayaks at the pier, crabbing, swimming, bare feet in the grass, and long evenings outside.
I love all of that. But after hosting here for many years, I’ve come to think winter is one of the most overlooked times to stay.
The leaves are down, opening up even more of the water views. There are fewer boats on Broadwater Creek. Winter sunsets come early, so you don't have to wait until late evening to see the sky turn pink, orange, lavender, or sometimes a combination that sends everyone looking for their phones.
And winter brings some visitors we don't get in quite the same way during the rest of the year: large numbers of migrating geese, ducks, and, some years, beautiful white swans.
One couple staying in our Sunrise Suite for Valentine's Day got an especially good show:
“We absolutely LOVED staying at Shawn’s paradise sunrise suite. Beautiful and comfortable, excellently stocked and we got the bonus of seeing (and hearing) migratory geese and swans off the balcony. Just a lovely lovely weekend to celebrate Valentine’s Day. ❤️❤️ We will be back for sure!”
— Kimberly, February 2026
Winter is a genuinely different experience here.
On a summer morning, there may be boats going by, people heading out in kayaks, kids on the lawn, or someone checking a crab pot.
On a winter morning, you're more likely to be inside with coffee, looking through the windows at birds on the water.
A February guest staying in our Waterfront Wonder Cottage described almost exactly that:
“The Cottage was in a unique location. Right on the bay, the mornings were lovely watching the geese and having coffee from the living room.”
— Jenny, February 2026
That's one of the reasons the property works especially well in winter: you don't have to be outside to experience the waterfront.
The Sunrise Suite has a private balcony and expansive water views. The Sky-Lit Flat + Solarium has skylights, a wall of windows in the Solarium, and its own balcony. The Cottage puts the water right outside the living areas. And Chesapeake Paradise House has water views from much of the house, including the large living and gathering spaces.
So when it's 35 degrees outside, nobody has to pretend that's perfect kayaking weather. You can be warm inside and still watch what is happening on the creek and Bay.
Birdwatching wasn't something I originally set out to make an “amenity” at Chesapeake Paradise. The birds simply came with the place.
Winter makes them particularly hard to ignore.
Guests see and hear migrating geese from the balconies and windows, ducks move through the creek, and swans sometimes appear on the water. We've had winter guests specifically mention the birds in their reviews — including people who weren't necessarily coming here as birdwatchers.
The open water and large windows also make it easy to watch without bundling up and heading somewhere else. Bring binoculars if you're serious about it, or just look up from breakfast when several dozen geese suddenly announce themselves outside.
This is one of the best reasons I know to visit Chesapeake Paradise outside the traditional vacation season.
The sunrises and sunsets here are beautiful year-round, but winter has its own advantages. The bare trees reveal more sky, and the early sunsets mean you're likely to be here and awake for them instead of waiting until 8:30 at night.
Some evenings are soft and pastel. Others are intense pink, orange, red, and purple. When the water is calm, the color reflects across the creek.
And you don't necessarily have to put on a coat to see it.
Depending on where you're staying, you may be watching from the Sunrise Suite, the Solarium, a living-room window, or your bed. If the weather cooperates, of course, you can also walk down to the pier.
A January guest who stayed in the Flat wrote:
“The sunrise/sunset views are absolutely stunning! It is close to Annapolis, yet secluded enough for complete relaxation.”
— Carlyle, January 2026
A family who spent Christmas here said the same thing:
“What a wonderful way to spend our Christmas vacation. The sunrises and sunsets were beautiful.”
— Lisa, December 2025
I'll admit that a hot tub beside the water makes considerably more sense to me when it's cold outside.
Our 4–5 person hot tub overlooks the water and is available year-round when weather and operating conditions permit. Depending on which accommodations are occupied, it may be shared with other Chesapeake Paradise guests.
We intentionally keep it a quiet-use area rather than a party hot tub. Guests use it for soaking, talking, reading, looking at the moon and stars, or warming up after being outside.
Renee stayed in the Flat in February and put it simply:
“The loft is a very peaceful place to stay, even in the winter! We enjoyed the views from the solarium and the sunroofs. The hot tub is very nice treat in the winter.”
That combination — cold air, hot water, and the Bay a few yards away — has made the hot tub one of our most popular winter amenities.
An older version of this article described our Maryland winters as mild.
I'm taking that out.
Sometimes they are. Sometimes they aren't.
We've had 50-degree winter days when people happily sit outside, and we've had snowstorms and stretches of serious cold. If you're planning a winter waterfront getaway in Maryland, check the forecast and pack accordingly.
The good news is that the property was designed to be enjoyed from indoors as well as out.
Chesapeake Paradise LITE has a gas fireplace. Waterfront Wonder Cottage has a wood-burning fireplace. We also have outdoor fire pits, with firewood available for the wood fire pit.
And occasionally winter gives us something completely unexpected.
One family arrived just after a major February snowstorm in 2026. During an unusual period of extreme cold, the water froze. Their review described the snow-covered property and frozen Chesapeake as “magical.”
That was an exceptional weather event, not something we expect or recommend planning around. But their experience illustrates something I've seen repeatedly: winter weather doesn't necessarily spoil a Chesapeake Paradise stay. Sometimes it becomes one of the things guests remember most.
Another group arrived immediately after a January snowstorm and wrote:
“The views were spectacular even in the freezing winter month of January. Absolutely great experience all the way through!”
— Ashley, January 2026
One thing people sometimes don't realize about Chesapeake Paradise is that you don't have to rent the whole property.
There are five different ways to stay, which makes a winter getaway possible whether you're coming alone to write for a few days, planning a romantic weekend, bringing the family, or gathering a larger group.
Our spacious upstairs king suite has a huge en suite bath, private balcony, and some of the property's best Bay views.
It's an especially good fit for a couple, a solo retreat, or anyone who wants the water view without renting an entire house.
This is the suite where our Valentine's Day guests watched and listened to the migrating swans and geese from their balcony.
The Flat Plus is a private upstairs apartment with a separate secure entrance. It includes the skylit studio area, wet-bar kitchen, marble bath and shower, queen and full beds, balcony, and the window-filled Solarium bedroom.
For winter, the Solarium may be the star. You can watch the water and sky through the windows while staying completely warm indoors.
The Cottage is a separate 3-bedroom, 2-bath house with heart-pine floors, a full kitchen, washer and dryer, and a wood-burning fireplace.
It's a good choice for a small family, several friends, or a couple who simply wants more room. It's also dog-friendly, so nobody has to explain to the dog why everyone else got a winter vacation.
CP LITE gives families and groups 4–5 bedrooms and 3 bathrooms, including the Sunrise Suite, plus the main living and dining areas, full kitchen, screened porch, deck, and balcony.
The separate upstairs Flat may be occupied by another party during a CP LITE stay, but each accommodation has its own private space and secure access.
For a larger family or group, the full Chesapeake Paradise House provides 6–7 bedrooms and 4 bathrooms, along with the screened porch, decks, balconies, yard, and pier.
It's especially useful when people want enough room to gather for meals and games without spending an entire winter weekend piled on top of one another.
One January group described exactly that:
“There were plenty of spaces to gather or take time alone, which was really important for our group. The kitchen was well stocked, and we had an easy time cooking our meals.”
— Ami, Washington, DC
Winter weekends here tend to work particularly well for couples because you don't need an itinerary to fill the time.
You can go into Annapolis for lunch, shopping, or sightseeing and come back to the water. You can pick up dinner from one of our local restaurants or cook in. You can watch a movie, soak in the hot tub, sit by the fireplace, walk around the property, or take coffee back to bed and watch the creek through the windows.
For Valentine's Day, anniversaries, birthdays, or a weekend away without a particular occasion, the Sunrise Suite and Flat Plus are our two smaller options.
And if you're comparing a hotel room in Annapolis with staying farther south on the water, it's worth considering what you want the weekend itself to look like. Annapolis is close enough to visit easily, while Chesapeake Paradise gives you a very different setting to come back to.
Winter also happens to be one of my favorite times to recommend Chesapeake Paradise to writers, artists, people working remotely, or anyone trying to finish something without the normal distractions at home.
There's strong Wi-Fi, tables and workspaces, lots of natural light, and enough room in several of the accommodations to change locations during the day.
You can work at a table overlooking the water in the morning, take a walk outside, make lunch, and move somewhere else for the afternoon.
Or don't work at all. I'm not your supervisor.
We've hosted people who come specifically for retreats and reflection as well as guests who simply want a couple of days away from their normal routine. Winter is especially well suited to both.
Quite a bit, although the list is different from July.
Depending on the weather, guests can:
~ Watch migrating geese, ducks, and swans
~ Photograph winter sunrises, sunsets, and reflections on the water
~ Use the waterfront hot tub when operating conditions permit
~ Sit around an outdoor fire pit
~ Enjoy the indoor fireplaces in accommodations that have them
~ Walk the two-acre property
~ Stargaze from the yard or pier
~ Read, play games, cook together, or watch movies
~ Work remotely or turn a few days into a personal writing or creative retreat
~ Visit Annapolis for restaurants, shopping, history, museums, and events
~ Explore nearby waterfront towns and restaurants
~ Bring the family together somewhere with enough room to spread out
Kayaks and the canoe are available on the property, but cold-weather water activities are naturally dependent on conditions and experience. Winter is not the season when we encourage people to prove how adventurous they are.
Summer weekends around the Chesapeake are popular for obvious reasons.
Winter doesn't have the same demand, and that can make it an especially good time to check rates and availability — particularly if your dates are flexible or you can come during the week.
Rather than publishing a discount here that may be outdated by the time you read this, check our direct-booking website for current rates, availability, and any seasonal offers.
You can also compare the five accommodations rather than paying for far more space than you need.
A couple may find that the Sunrise Suite or Flat Plus is exactly enough. A family might prefer the Cottage. A group can move up to CP LITE or the full Chesapeake Paradise House.
If your idea of a getaway requires swimming, warm-weather boating, and spending the entire day outdoors, come see us in summer.
It's wonderful here then.
But if you're looking for a winter waterfront getaway in Maryland where you can see the water from inside, watch birds and changing skies, soak in a hot tub, sit near a fireplace, spend time with someone you love, or simply have a few days with fewer plans, don't automatically wait for spring.
Our winter guests keep reminding us of that.
One called the Flat “a very peaceful place to stay, even in the winter.”
Another watched geese over morning coffee.
Another celebrated Valentine's Day with swans outside the balcony.
A January guest said the views were spectacular even in freezing weather.
And one of my favorite short winter reviews may say it best:
“Very peaceful. Pictures can't express how beautiful relaxing and fun this stay was!”
— Adrian, January 2026
I've been sharing this little corner of the Chesapeake Bay with guests since 2009, and every season has things I love about it.
Winter deserves a place on that list.
Chesapeake Paradise is located in Deale/Churchton, Maryland, on Broadwater Creek near the Chesapeake Bay and a short drive from Annapolis.
Choose from five waterfront accommodations, from the Sunrise Suite for two to the full 6–7 bedroom Chesapeake Paradise House for families and groups.
Check current availability, rates, and seasonal offers on our direct-booking website.
Shawn
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