Piney Point Harbor Haven image 1
Piney Point Harbor Haven image 2
2nd Floor Living Room area w/ large Lovesac sectional.
Piney Point Harbor Haven image 4
Piney Point Harbor Haven image 5

Piney Point Harbor Haven

3 bedrooms·3½ baths
Piney Point • Maryland
4.97(32 reviews)

$1,455.19 USD $1,340.98 USD total for 3 nights

Nov 8 – 11, 2026

Sunrise Bay Retreat • Private Beachfront
Sunrise Bay Retreat • Private Beachfront
Sunrise Bay Retreat • Private Beachfront
Sunrise Bay Retreat • Private Beachfront
Sunrise Bay Retreat • Private Beachfront

Sunrise Bay Retreat • Private Beachfront

4 bedrooms·4 baths
Scotland • Maryland

$1,675.75 USD total for 3 nights

Nov 8 – 11, 2026

Sunrise Bay Retreat • Private Beachfront
Sunrise Bay Retreat • Private Beachfront
Sunrise Bay Retreat • Private Beachfront
Sunrise Bay Retreat • Private Beachfront
Sunrise Bay Retreat • Private Beachfront

Sunrise Bay Retreat • Private Beachfront

4 bedrooms·4 baths
Scotland • Maryland

$1,521.25 USD total for 3 nights

Nov 8 – 11, 2026

Ivy Cove
Ivy Cove
Ivy Cove
Ivy Cove
Ivy Cove

Ivy Cove

3 bedrooms·2 baths
Lusby • Maryland
4.99(131 reviews)

$1,176.60 USD total for 3 nights

Nov 9 – 12, 2026

*Where Eagles Soar* Peaceful Waterfront Retreat. image 1
*Where Eagles Soar* Peaceful Waterfront Retreat. image 2
The perfect place to unwind, share stories, and make memories!
The true heart of the home is our spacious sunken living room. Just one step down from the kitchen and dining area, this space wraps you in cozy comfort and is the ultimate spot to unwind. The water views, gorgeous sunsets, wildlife are unbeatable!
*Where Eagles Soar* Peaceful Waterfront Retreat. image 5

*Where Eagles Soar* Peaceful Waterfront Retreat.

2 bedrooms·2 baths
Cobb Island • Maryland
4.97(105 reviews)

$941.85 USD total for 3 nights

Nov 9 – 12, 2026

Hickory House on the Chesapeake Bay! image 1
Hickory House on the Chesapeake Bay! image 2
Hickory House on the Chesapeake Bay! image 4
Hickory House!
Hickory House on the Chesapeake Bay! image 6

Bay Views, Private Beach Access and Pet Friendly!

2 bedrooms·1 bath
Saint Leonard • Maryland
4.92(88 reviews)

$647.00 USD total for 3 nights

Nov 8 – 11, 2026

Cozy 5-Bed Retreat, Heated Spa
Elegant brick home with glowing entry and stunning autumn curb appeal
Convenient in-home laundry room with washer, dryer, iron, and folding space
Cozy 5-Bed Retreat, Heated Spa
this is the Blue Room. The Decour is inspired by grand millennial chinoiserie. Daylight above is a remote controlled fandelier for climate comfort.

Cozy 5-Bed Retreat, Heated Spa

5 bedrooms·3½ baths
Port Republic • Maryland
4.78(58 reviews)

$1,680.50 USD total for 3 nights

Nov 9 – 12, 2026