Bring your own wood to enjoy the Solo Stove firepit. Use caution as the metal stove gets extremely hot. A fire should never be left unattended.
Enjoy eating outside and a view of the water and sunset from the patio.
A beautiful summer evening in the yard overlooking the marina and waterfront.
This 3-season sunroom offers views of the water and community beach area.
The living room provides a gathering space to read, watch TV (Netflix, Disney+, and Hulu with live streaming), or take a nap.

The Bohemia Charmer

4 bedrooms·2 baths
Earleville • Maryland
4.96(115 reviews)

$890.00 USD total for 3 nights

Nov 16 – 19, 2026

Early morning on the tip of the Chesapeake
Waldins Chesapeake
Front Deck
Waldins Chesapeake
Waldins Chesapeake

Waldins Chesapeake

3 bedrooms·2 baths
Perryville • Maryland
4.93(54 reviews)

$1,734.90 USD total for 3 nights

Nov 12 – 15, 2026

The sunsets are amazing from you own private deck!
The river is beautiful in the fall.
Beautiful Fall colors from our peer
Enjoy a cozy waterfront Christmas in front of the fireplace
Christmas Season at Serenity is so peaceful!

Breathtaking Waterfront Home/ Amazing sunsets nightly! Book Christmas now!

4 bedrooms·2 baths
Elkton • Maryland
4.84(19 reviews)

$2,012.00 USD total for 3 nights

Nov 12 – 15, 2026

Stepping into our family room feels like entering a cozy art gallery! The antique pieces tell stories of the past, and the velvet sofa is so inviting. Curl up here for movie nights on the large screen TV. It's the perfect blend of modern and cosy.
Bedrooms with king bed.
Living room with view to private brick patio.
Large entry/ dining room with gas fireplace.
Well equipped kitchen.

Gorgeous home in town center & short walk to WAC

5 bedrooms·3 baths
Chestertown • Maryland
5(227 reviews)

$1,113.00 USD total for 3 nights

Nov 15 – 18, 2026

Stunning 9 Bedroom Villa on the Chesapeake Bay image 1
Stunning 9 Bedroom Villa on the Chesapeake Bay image 2
Stunning 9 Bedroom Villa on the Chesapeake Bay image 3
Stunning 9 Bedroom Villa on the Chesapeake Bay image 4
Stunning 9 Bedroom Villa on the Chesapeake Bay image 5

Stunning 9 Bedroom Villa on the Chesapeake Bay

9 bedrooms·6½ baths
Rock Hall • Maryland
5(6 reviews)

$5,915.00 USD total for 3 nights

Nov 12 – 15, 2026