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Featured Holiday Homes in Piney Point

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!

St Inigoes
Located in Saint Inigoes, this vacation home is on the waterfront, a 3-minute drive from Saint Inigoes State Forest and 7 minutes from Cardinal Gibbons ...
Screened Patio, Deck & Grill: Saint Inigoes Home!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard
With a stay at this vacation home in St. Leonard, you'll be near the beach, just steps from Jefferson Patterson Park and Museum and a 3-minute drive from Perigeaux ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Ridge
With a stay at this vacation home in Ridge (Point Lookout), you'll be within a 10-minute drive of Confederate Memorial Park and Cardinal Gibbons Park.
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
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Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Heathsville
Located in Heathsville, this vacation home is on the waterfront, within a 15-minute drive of Ginny Beach and Smith Point Marina.
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Belle of the Chesapeake Bay

Belle of the Chesapeake Bay

Lusby
When you stay at this vacation home in Lusby, you'll be within a 10-minute drive of Cove Point Park and Calvert Cliffs State Park.
Belle of the Chesapeake Bay
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Lusby
Located in Lusby, this vacation home is by the ocean, a 4-minute drive from Drum Point Lake and 5 minutes from Seahorse Beach.
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Sea Glass Beach House!  Large sand beach, dock and hot tub! Pets welcome!

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Hague
Located in Hague, this vacation home is by the ocean, within a 15-minute drive of Coles Point Marina and Hague Winery.
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Lusby
Located in Lusby, this vacation home is on the waterfront, a 1-minute drive from Vera's White Sands Marina and 9 minutes from BGE Field.
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

Mechanicsville
Located in Mechanicsville, this vacation home is on the waterfront, a 5-minute drive from Cape Saint Marys Marina and 8 minutes from John Baggett Park at Laurel ...
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Piney Point Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Piney Point vacation homes are the perfect way for you to wing it.

Holiday houses in Piney Point let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Piney Point in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Piney Point adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Piney Point with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Piney Point vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Piney Point Holiday Homes essential information

Accommodation
149 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Screened Patio, Deck & Grill: Saint Inigoes Home!, Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks, Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10, Belle of the Chesapeake Bay, Waterfront Lusby Retreat w/ Deep-Water Dock & Slip, Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! , Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat, Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

Top trending hotels in Piney Point

Island Inn & Suites, Ascend Hotel Collection

Island Inn & Suites, Ascend Hotel Collection

3 out of 5
16810 Piney Point Road, Piney Point, MD
A stay at Island Inn & Suites, Ascend Hotel Collection places you in the heart of Piney Point, within a 5-minute drive of Saint George Island Beach and Piney ...
Island Inn & Suites, Ascend Hotel Collection
Waterfront Cottage in Piney Point w/ Kayaks!

Waterfront Cottage in Piney Point w/ Kayaks!

Piney Point
Located in Piney Point, this cottage is on the waterfront, a 1-minute drive from Saint George Island Beach and 5 minutes from Jimmy Island.
Waterfront Cottage in Piney Point w/ Kayaks!
Quaint fishing retreat on the lower Potomac Piney Pt

Quaint fishing retreat on the lower Potomac Piney Pt

Piney Point
Located in Piney Point, this vacation home is on the waterfront, within a 5-minute drive of Potomac River and Piney Point Beach.
Quaint fishing retreat on the lower Potomac Piney Pt
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Piney Point, private , Beach Front Cottage

Piney Point, private , Beach Front Cottage

Piney Point
With a stay at this cottage in Piney Point, you'll be steps from Piney Point Beach and a 2-minute drive from Piney Point Lighthouse.
Piney Point, private , Beach Front Cottage
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.