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Vacation Rentals in Point Lookout, Maryland

about Point Lookout

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Point Lookout, Maryland vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Point Lookout are added and updated every week!

Compared to hotels, Point Lookout vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Point Lookout, Maryland Vacation Rentals and Tourism

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Point Lookout things to do


The Tides Inn

I'm rating the Chesapeake Club at The Tides Inn, not the whole Inn itself. Had lunch here with my family on a lovely Monday afternoon. Well, it was hot more


Point Lookout State Park

A very nice park. Each campsite has a very nice pad for tents, a fire ring, and a picnic table. The rest rooms are very nice and very clean. I loved more


Slack Winery

We were camping in the area that weekend and saw the wine sign. We decided to go for wine tasting Sunday afternoon. Slack Winery property is beautiful! more


Port of Leonardtown Winery

Great afternoon! Went here with another couple as part of a Groupon. We each got the tasting, glasses and a bottle of wine. I tend to like VA wines more more


Flag Ponds Nature Park

We look forward to visiting Flag (as we call it). This is probably the nicest swimming beach on the Chesapeake Bay (at least the nicest I have more


General's Ridge Vineyard & Winery

My girlfriend and I stumbled upon this place while we were vacationing on the Northern Neck some time ago. We're from upstate New York, and as such, we more


Warrior Dash

For never having done one it was fun!!! It was so much fun!!! They held it on the dirt bike race park so yes you were running up and down the tracks more


Calypso Bay Crab House

This has nothing to do with the food, but rather the late-night booty-shaking experience. Unlike the other reviewer, I am a closet fan of more


Historic St Mary's City

Fun place to go for everyone! History in action with workers in costume and reconstructed buildings, active archeological sites, relaxing more


Sailwinds Park

Our annual rest stop. 2 hours from home on the way to Ocean City, MD. Clean bathrooms. Great view & if you have children, a great little park for more


Point Lookout Lighthouse

On a spit of land far on the tip of St. Mary's county where the Chesapeake and the Potomac literally collide, sits the small, weather worn and more


Patuxent Adventure Center

So these guys sell bikes and repair them, but there is no rental. You can rent paddle boards and more


Bordeleau Winery

Wines as good as they get are here. And with great packaging and labels. Plus at reasonable prices. I never make a trip out this way in Maryland more


AMC St. Charles Town Center 9

Great seats! The theater was very clean both concessions and the actual theater. Love the idea of assigned seating. Great picture and sound in the more

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Chesapeake Charm - Fishing, Crabbing, Boating & Chillin'
Point Lookout House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $200 - $300 /nt
    $1,400 - $1,750 /wk

36 reviews write a review

Creekside Hideaway
Point Lookout House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $200 - $350 /nt
    $1,400 - $1,900 /wk

6 reviews write a review

Vintage Beach Cottage
Point Lookout Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $300 /nt
    $1,750 /wk

5 reviews write a review