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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 150 Vacation Homes in Piney Point with updated reviews, rates, and availability.

Screened Patio, Deck & Grill: Saint Inigoes Home!
Saint Inigoes Vacation Rental | 3BR | 2BA | 3 Steps to Enter | 1,456 Sq Ft

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
The driveway allows for plenty of parking for guests!

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

9.6 out of 10, Exceptional, (29)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Terrace/patio

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

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Great evening views!

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

9.8 out of 10, Exceptional, (32)
"Very nice and quiet. We were there end of December. "
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"Our granddaughters live in the neighborhood and our youngest was having her first birthday! It was just my husband and myself, way more house than we needed but tons more comfortable than a hotel. The winter views of the Bay from the living room were awesome. I highly recommend you make a cup of coffee and watch the sunrise. A few surprises with the house itself, the most egregious for me was the fireplace pictured is not functional. The hosts have done a nice job with this house and are still...
Belle of the Chesapeake Bay
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Lusby Vacation Rental | 4BR | 3BA | 1,872 Sq Ft | Stairs Required

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Sunrise on your private beach

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

10.0 out of 10, Exceptional, (17)
"Great stay, easy check-in/check-out, highly recommend"
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
Sit on the patio and enjoy your coffee in the morning.

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

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
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
living room, there is TV with netflix/ prime streaming.

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

10.0 out of 10, Exceptional, (11)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier
Stove top with a View !

Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

10.0 out of 10, Exceptional, (36)
"We wanted a family vacation and looked for a place on Chesapeake Bay. My son and daughter found this place and we reserved it. The house is beautiful. Has everything one would want. The location is great although it’s a bit of a drive to anywhere. Our plan was to spend most of the time at the house and in the bay. However that didn’t happen. First the weather didn’t cooperate as it rained most of the week. In addition there was an invasion of jellyfish. They were terrible! My grandchildren were...
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier
Virginia Retreat on Wicomico River w/ Dock!
Burgess Vacation Rental | 4BR | 2.5BA | 3,321 Sq Ft | Stairs Required to Access

Virginia Retreat on Wicomico River w/ Dock!

10.0 out of 10, Exceptional, (16)
"My mom didn’t want to leave. Beautiful family retreat. Quiet and restful. "
Virginia Retreat on Wicomico River w/ Dock!
18-Acre Waterfront Sanctuary: Peace & Privacy
Aerial view

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy
Secluded River Front Cottage
Property grounds

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
Ariel view of the house, dock and beautiful Chesapeake Bay.

Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

9.0 out of 10, Wonderful, (14)
"My family enjoyed our stay over Thanksgiving. Three generations with different needs and the house accommodated us well."
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
When you want to get away from everything Magnolia shores 2 acres of tranquility
Exterior

When you want to get away from everything Magnolia shores 2 acres of tranquility

10.0 out of 10, Exceptional, (65)
"Great time with great hosts! "
When you want to get away from everything Magnolia shores 2 acres of tranquility
Your private beach retreat in historic St. Mary's
Welcome to your private beach and pier!

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at this property. The house was in mint condition and had all the amenities we needed. Enjoyed the hot tub, kayaks, the fire pit, and the dock. Great place to spend a relaxing long weekend. "
Your private beach retreat in historic St. Mary's
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Scotland Vacation Rental | 3BR | 2BA | Stairs Required | 1,644 Sq Ft

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Luxury Modern Waterfront Retreat
★ Coziness & Outdoor ★ Gas fire-pit to enjoy your evening or wood fire-pit if you prefer the wood crackling sounds

Luxury Modern Waterfront Retreat

9.8 out of 10, Exceptional, (10)
"Very nice inside, love all the windows"
The price is AED 584
AED 1,715 total
includes taxes & fees
23 Jan - 24 Jan
Luxury Modern Waterfront Retreat
Bay Estate by AvantStay | Waterfront, Private Pond
Pier.

Bay Estate by AvantStay | Waterfront, Private Pond

10.0 out of 10, Exceptional, (1)
"Such a beautiful house, very nice for family or friends get together."
Bay Estate by AvantStay | Waterfront, Private Pond
Cottage on the Bay
Exterior

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay
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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Other property types in Piney Point

Waterfront Cottage in Piney Point w/ Kayaks!
Piney Point Vacation Rental | 3BR | 1.5BA | 2,484 Sq Ft | Stairs Required

Waterfront Cottage in Piney Point w/ Kayaks!

7.6 out of 10, Good, (4)
"First, this was a last minute booking, due to our inability to stay at our original rental. Becky was responsive to our needs so we could vacate our previous rental without delay. Next, what I loved about this property, and something you do not get very often is the amount of living, relaxing space there is in this rental. Several areas for groups of people to spread out, watch TV, look at the water, play games, often times while there are several bedrooms, there are precious few places for...
Waterfront Cottage in Piney Point w/ Kayaks!
Quaint fishing retreat on the lower Potomac Piney Pt
Views from the waterfront

Quaint fishing retreat on the lower Potomac Piney Pt

9.8 out of 10, Exceptional, (48)
"Had another nice getaway. Caught more fish than last time. Best sunsets around. Had a fire going in the evenings and hung out on the pier. Was a real nice way to end vacation season. "
Quaint fishing retreat on the lower Potomac Piney Pt
Piney Point, private , Beach Front Cottage
Beach

Piney Point, private , Beach Front Cottage

10.0 out of 10, Exceptional, (86)
"This house is beautiful and has everything anyone could ask for. The scenery is spectacular too. We enjoyed sitting outside watching the sun set, just listening to the water and enjoying a fire on the beach. The kitchen is any cook's dream! The owners are wonderful and communicated with us wonderfully. We would give it a 10 rating if possible and will certainly be back. One of our best vacations!"
Piney Point, private , Beach Front Cottage
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.