*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!
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*Where Eagles Soar* Peaceful Waterfront Retreat.

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

$1,014.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

Escape to the Riverpoint, this unique house embodies the charm of a Swiss chalet A-Frame, complemented by a picturesque boathouse on the serene Canal of the Port Tobacco River.
The hot tub is tucked under the deck which offers privacy. End your day soaking in the hot tub that can fit up to 7 people.
The fire pit is next to the river and in the center of a sand area making it feel like a little beach.
The backyard is fully-fenced in so everyone can enjoy the backyard comfortably
Watch your favorite films on this 85” Google TV in the basement movie room.

5BR Riverfront A-Frame

5 bedrooms·4 baths
Port Tobacco • Maryland

$2,014.81 USD total for 3 nights

Oct 29 – Nov 1, 2026

Oasis at Charity’s Hope Farm Resort image 1
Fun with inflatables on the beautiful salt water pool with whirlpool jets.
Oasis at Charity’s Hope Farm Resort image 3
Horse trainer works with our miniature horse and pony.
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Oasis at Charity’s Hope Farm Resort

5 bedrooms·3 baths
La Plata • Maryland
4.94(36 reviews)

$2,535.00 USD $1,601.00 USD total for 3 nights

Oct 27 – 30, 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

Oct 27 – 30, 2026

Ivy Cove
Ivy Cove
Ivy Cove
Ivy Cove
Ivy Cove

Ivy Cove

3 bedrooms·2 baths
Lusby • Maryland
4.99(130 reviews)

$1,176.60 USD total for 3 nights

Oct 27 – 30, 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)

$667.00 USD total for 3 nights

Oct 31 – Nov 3, 2026