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Piney Point Vacation Rentals

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Browse Select Piney Point Vacation Homes

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!

Charming 3-bedroom house with WiFi, AC in peaceful Reedville

2.0 star property
4.0 out of 10, (1)
The price is CA $214
CA $393 total
includes taxes & fees
Dec 28 - Dec 29
Charming 3-bedroom house with WiFi, AC in peaceful Reedville

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (19)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway

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

9.8 out of 10, Exceptional, (31)
"very quiet, peaceful, relaxing location. The house had everything we needed. We would definitely stay there again."
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

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

10.0 out of 10, Exceptional, (15)
"House is perfect for families to get together for a holiday. Has pretty much everything you need."
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

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

10.0 out of 10, Exceptional, (10)
"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

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!

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

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

Waterfront Maryland Vacation Home: Private Beach!

10.0 out of 10, Exceptional, (8)
"We had such a peaceful stay! We felt the love you put into your family’s farmhouse! It was perfect! You didn’t miss a detail! The view was beautiful and we enjoyed the beach as well! Thank you for providing the kayaks and bikes! Our experience truly was heaven on earth! We look forward to coming back!"
Waterfront Maryland Vacation Home: Private Beach!

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

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

9.8 out of 10, Exceptional, (9)
"A little had to trailer a boat to house but nice other then that "
The price is CA $228
CA $676 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Luxury Modern Waterfront Retreat

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

Riverside House w/ Kayaks, Piano & Fireplace

9.0 out of 10, Wonderful, (12)
"This house is well-maintained and my business associates enjoy staying here. We will book this house every time it comes available."
Riverside House w/ Kayaks, Piano & Fireplace

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

Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

9.4 out of 10, Exceptional, (3)
"We were in town for a reunion and this was a nice alternative to the local hotels. Updates to the house were nicely done and I love that checkout was simplified to two to three tasks, not a whole laundry list. If I had two suggestions, one would be that the plug-ins were too many and too strong - we considered opening a window for some relief but did not since we were out at the reunion most of the day. But only one per floor would likely be enough although the house is so clean (five stars!)...
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

Waterfront Leonardtown Retreat w/ Dock Access!

10.0 out of 10, Exceptional, (1)
"We had a wonderful time. My husband spent the days crabbing from the pier, my brother fishing from the pier. We all went out kayaking. Beautiful sunsets. Enjoyed a crazy night of ping pong, playing cards and online Jackbox games. Plenty of space and loved the large kitchen and bathroom for every bedroom. None of us wanted to leave."
Waterfront Leonardtown Retreat w/ Dock Access!
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!

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

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

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.