Vacation Rentals By Owner In Piney Point, MD

This southern Maryland location is filled with charm and history. St. George Island is site of the first battle in Maryland of the Revolutionary War. Come enjoy the water and peaceful scenery. There are no crowds and need for clocks. Take in the beautiful sunrises each morning and make your own schedule of reading in a hammock, sea glass searching on the beach, walking on a one lane road between high grasses, biking off the island using the bike lane or boating in front of the property on the quiet 1 1/2 mile expanse of St. George Creek. The Ruddy Duck Restaurant is an easy walk with fantastic sunset views. If you are a history buff you will enjoy Sotterly Plantation and Point Lookout Park.br Bedroom 1br Double bed with 1/2 bath and antennae TVbr Bedroom 2br Queen bed with antennae TVbr Bedroom 3br Queen bed with Water viewbr Bedroom 4br Master bedroom queen bed, twin bed, trundle, antennae TV, attached bath, new deck with water viewbrbr Queen size pullout sofa with three ceiling fans, French doors and sunrise view.brbr There is no cable TV but there are plenty of games and books.brbr brThere is a garage apartment that is rented separately for 2 people on the property.

Charming Waterfront Escape with beach and pier for fishing and crabbing

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(12)

$997.23

Welcome to your dream vacation home, an exceptional waterfront estate nestled in the exclusive Piney Point. This exquisite residence, set against the tranquil backdrop of the Potomac River, epitomizes luxurious living. Meticulously designed, this five bedroom, three bathroom masterpiece combines elegance and comfort in every corner.brbrUpon entering, you are greeted by an expansive open-concept living area that boasts panoramic views of the river. Massive windows flood the space with natural light, creating a seamless flow between the indoors and the breathtaking outdoors. The chef's kitchen is a true highlight, featuring high-end appliances, custom cabinetry, and a spacious island ideal for entertaining. The Kitchen Nano Wall opens to the outside creating and outdoor indoor space perfect for entertaining and enjoying the Pool, deck area seamless transition. The inviting living room, with its stunning water views, creates the perfect space for relaxation, while the formal dining area exudes sophistication.brbrThe home’s thoughtful layout includes two opulent primary suites, each offering an abundance of space, walk-in closets, and spa-like bathrooms. The gym has everything you need for your daily work out. Living room /den with its 85 inch television for movie nights and to unwind to your favorite shows. brThe luxury finishes throughout the home, including rich hardwood floors, intricate moldings, and designer fixtures, elevate the living experience.brbrStep outside to a world of unparalleled beauty. Almost an acre, this estate offers direct access to the Potomac River, with a private sandy beach perfect for enjoying peaceful sunsets or launching your boat for a day on the water. Swimming Pool and large deck for playing with the kiddos and or entertaining guests. A detached two-car garage. The lush, meticulously landscaped grounds provide both privacy and beauty, with expansive views of the Potomac RiverbrbrThis estate is perfectly positioned to offer both seclusion and convenience, just a short drive from dining, shopping, and essential amenities.brbrThe Property sleeps 10 guests comfortably, 2 additional twin sized beds can be made available upon request for a total of 12 guests. broutdoor area with gas grill, ping pong table, lounge chairs to enjoy long afternoons with family and friends grilling and unwinding. Gas Grill, 3 kayaks, 3 bikes.

Stunning luxury waterfront beach house 90 minutes from the Nations Capital.

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(5)

$247.49

Unwind in Piney Point at this lovely waterfront cottage. With two full beds in bedroom 1 and one queen-size bed in bedroom 2, and a cozy living room with a sofa bed, this property is perfect for small groups or families. Enjoy the convenience of WiFi, a hair dryer, and a washer and dryer during your stay. The bathroom is equipped with all the essentials you need. We think our place will help you experience everything Piney Point has to offer. Additionally, enjoy kayaking, fishing, crabbing from the shared pier, as well as grilling, riding bikes, and playing outdoor games like cornhole and horseshoes.

Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(25)

$169.79

Welcome to The Love Shack – Your Cozy Piney Point EscapebrbrThis house is on its own piece of property, fully fenced in and does not share a yard. brbrTucked away in charming Piney Point, this inviting studio is the perfect hideaway for couples, small families, or solo travelers. Featuring a plush queen bed and a comfy pull-out sectional (also queen-sized), this 1-bedroom retreat is designed for rest, relaxation, and a touch of fun.brbrYou’ll find all the comforts of home, including WiFi, air conditioning, and a washer for extended stays. Need local tips or hidden gems to explore We’re just a message away and happy to help make your trip unforgettable.brbrStep outside to your own private outdoor oasis—roast marshmallows by the fire pit, soak under the stars in the hot tub, or fire up the electric grill for a laid-back dinner. The friendly neighborhood is both people- and pet-welcoming, with parking available for boats and an easy launch less than a mile away. Traveling with bikes Let us know at booking, and we’ll arrange extra storage.brbrYour peaceful getaway awaits—come unwind at The Love Shack.

Apartment

Tiny, Funky, and Full of Love - Welcome to the Love Shack

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(20)

$606.59

Southern Maryland Treasure - Peaceful retreat with lots of room for large family gathering or weekend getaway. Enjoy beautiful views, crabbing, fishing, kayaking, paddle boarding and so much more!!!!!brbrHome has a beautiful wrap around porch to watch the one of a kind sunsets, enjoy morning coffee, sit and read a book or watch the kids play in the large yard. There is even more outdoor seating around the firepit to enjoy your evenings reminiscing and telling stories with a glass of wine.brbrFeel at home in large, fully stocked kitchen. Long Kitchen table that seats 12, in addition to the counter bar that has 4 bar stools. Living room equipped with a stereo system also hooked up to surround sound. There is office space for those that need to get any work done while trying to vacation. brbrMaster bathroom includes a spa tub and full shower. Other two bathrooms have walk in showers. Lots of closet space. Washer and Dryer available for use. Additional large freezer if needed too (usually stocked with chicken necks for crabbing off the pier, reach out for more details if you need them)brbrWe look forward to having you! You won't be disappointed!!

WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(3)

$214.91

Welcome to St. George’s Getaway, a relaxing and family-friendly escape! This warm, inviting home is perfect for families, couples, or small groups looking to unwind and make lasting memories.brbrStep inside to a bright and comfortable living space featuring cozy furnishings, modern touches, and everything you need for a stress-free stay. The fully stocked kitchen makes home-cooked meals a breeze, and the back yard with a firepit is perfect for gathering together after a day of adventures!br1) Non-Smoking Property.br2) Check-in time is 4pm or later on your arrival date. Want to check-in early We`ll let you check-in two hours before the scheduled check-in time! 2pm check in $30 or 11am $60. This fee goes to our amazing cleaners! This must be agreed to and paid for before your stay.br3) Check-out time is 10 am. Need some time to sleep in Go for it! With late check-out we`ll give you two more more hours from the scheduled checkout time before you have to go! 12pm check out fee is $30 or 1pm check out fee is $50. This fee goes to our amazing cleaners. This must be agreed to and paid before your stay. The house must be vacated by check out time and doors locked. The house should be left clean, and all trash should be removed and placed outside in the trash bin. br4) Maximum occupancy of the property is listed on contract and MUST not be exceeded. Guest agrees that exceeding maximum occupancy is a material breach of this Agreement and will result in immediate removal and forfeiture of all monies paid. brbr5) No Bachelor, Bachelorette, Sorority or Fraternity parties chaperoned or not, are permitted. ABSOLUTELY NO HOUSE PARTIES ALLOWED. Violation is a material breach of this Agreement and will result in the immediate termination of the Guest’s visit without refund, with no exceptions. brbr6) Locked areas for which the Guest is not provided a key, such as the owner`s personal storage areas, are exempt from this Agreement and are off-limits to the Guest. Forced entry into these areas is cause for immediate eviction and Guest will be charged for any damaged or missing items.brbr7) House comes equipped with internet access. If any charges occur on the owner’s Internet service, Guests will be billed for the charges, plus a $100.00 collection fee. brbr8) House comes equipped with furniture, kitchen appliances, pots and pans, dishes, glassware, silverware, pillows, towels, linens, blankets, bedspreads and basic housekeeping items. Guests will be furnished with a starter amount of bathroom, kitchen, and laundry products unless otherwise indicated in the description of the house. Guest agrees to use bed linens (sheets and pillowcases) on all bedding being used during their stay. Cribs are not provided.brbr9) Guest shall not deliberately or negligently destroy, deface, damage or remove any part of the premises, nor render inoperable the smoke detectors provided by the Owner, or knowingly permit any person to do so. Guest must notify Owner of the need for replacement of or repairs to the smoke detectors. brbr10) Owner is not responsible for items left by Guests. If an item is left behind you will be charged for a postage fee to return such item. brbr11) This house is a non-smoking house. If you smoke in the house, you will be charged an additional $400.00 for cleaning of the house entirely to rid it of smoke.brbr12) Want to bring your pet(s) along Request to bring your pet(s) here! Prices are PER day. brbr1st pet $30 PER day. br2nd pet $20 PER day.

St George`s Getaway W/ Firepit!

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$183.15

Enjoy the lovely setting of this romantic spot in nature. This tiny house you have one queen bed and one bunk bed. You will have full access to our private beach at a different address on the island. There, you can relaxed, fishing, crabbing, and picnic. The address for the private beach is at 16431 Thomas Road with fence and gated with sandy beach. You can google it as St. George Island Beach.

Tiny House at St. George Island

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(55)

$201.17

Welcome to Wollongong, our Potomac Oasis!brbrWe are a NEWLY RENOVATED fishing retreat directly on the shores of Historic St. George’s Island, MD, on the Lower Potomac. Catch absolutely brilliant 180º sunsets from our patio or private dock, and cozy up by our firepit!brbrThough our cottage is small, it sure is cozy and totally functional for short or long-term rentals. We have a full kitchen, washer/dryer, 2 bedrooms, linens + towels, cooking essentials (salt & pep, oil, pots/pans, coffee, spices), crab pots, A/C to accommodate a quaint and peaceful getaway. Large dock to fish for Rockfish & crabbing. Half mile to boat ramp access to St Marys & Potomac Rivers, with the Chesapeake & Pt Lookout 8-10 miles south.brbrPlease call text or email with any questions, concerns, or comments. We aim to accommodate your needs as best we can!

Quaint fishing retreat on the lower Potomac Piney Pt

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(86)

$640.9

Welcome to an exceptional private home on St. George Island--just 1.5 hours from Washington, DC (without going over the Bay Bridge!). This River Run property sits on 3 acres for the best in privacy, relaxation, and recreation. At this location, upriver from the Chesapeake Bay, the Potomac River is 4 miles wide, providing an exquisite vista and lots of opportunities for water activities. The 150 ft. pier with built-in benches is perfect for morning coffee, crabs for lunch, spectacular evening sunsets, fishing and checking for crabs in the pots attached to the pier – rods, reels and crabbing equipment provided. Various sizes of life jackets are provided. There is a nearby public ramp to launch your boat or personal watercraft. Solomons Island (popular weekend destination with boat/jet ski rentals) and wineries are within a 30 minute drive.brbrThe private beach is great for sunning, reading, launching kayaks and paddle boards. Kids will have lots of fun playing in the sand and collecting sea glass. Beach toys and floats are provided. The huge screened-in porch is great for dining, chatting, or quietly enjoying the views. There is an indoor, heated (non-diving) swimming pool, and the pool room comes complete with a popcorn machine (popcorn supplied) and a commercial frozen drink machine for Slushies and margaritas (alcohol not provided). Pool toys are provided.brbrOutside there is ample room for volleyball, badminton, cornhole toss, croquet, bocce, horseshoes and barbecuing (provided). An old-fashioned tree swing is available as well as two full- size hammocks suspended from nearby trees. The outdoor shower also has a gorgeous water view. Plenty of wood is provided for the fire-pit on the beach which is a great conversation spot, and fun for roasting hot dogs and toasting marshmallows, utensils provided. Included, for your pleasure is a kayak, canoe, and two stand-up paddle boards. A variety of other pool/beach toys are also available for your fun.brbrThe pier has a boathouse on which there is an osprey nest and usually occupied. Other wildlife which may be observed on occasion includes bald eagles, heron, seagulls, deer, fox, rabbits, and squirrels. Smaller birds usually visible include hummingbird, robin, redbird, bluebird, woodpecker and many others. Our friendly community cat CC is also likely to visit you if you choose to say hi to him or feed him. In the water you may see dolphin, skates, sea horses, and many variety of fish. September and October are excellent months for crabs.brbrCheck in is at 4:00 pm. Check out at 10:00 am. A four-digit code will be configured in the digital locks at both entrance doors prior to arrival. This feature eliminates lost keys, lockouts, etc.brbrThe 1st floor has a Master Bedroom suite with full bath and sleeps two. This level has an open floor plan, including a large family room, dining room and kitchen, all with river views. The main laundry and a powder room are on 1st floor. In addition, there is a pool room bath with shower on the 1st floor. A stair lift is available to use from the 1st floor to the 2nd floor. Upstairs is another family room with vaulted ceiling, another full kitchen, personal laundry, bedrooms and a private deck with spectacular views. The kitchens are equipped with range, refrigerator, microwave, and Keurigs, regular coffee makers, silverware, and dishes. A Pack-N-Play, booster seat and high chair are also provided upon request.brbrOn the 2nd floor there are 3 bedrooms: a master bedroom (queen size) with an HDTV and a private bath, a queen bedroom, and a room with a full size bed. In the upstairs family room there is a queen sleep sofa and a twin convertible ottoman bed, for an upstairs sleeping capacity of nine. There is a 2nd floor hall bath with a tub/shower. Bed linens, towels, beach towels, and laundry detergent are provided. There is independent air conditioning on each floor.br brBoth family rooms are equipped with flat screen HDTVs, Blu-ray players and cable television. High speed Internet Wi-Fi is available throughout the house. Outdoors and adjacent to the house with a short walkway there is a large enclosed shower with hot and cold water, and at the steps to the beach there is a cold water shower to rinse off.brbrFor child safety, the sliding glass door from the family room to the pool room has a lock at the top which is reachable to adults but not children. Please note that young children need to be supervised as the house is not child proofed. Electrical outlets are not covered and there are no child locks on kitchen or laundry cabinets. Having said that, all window and door blinds are Levelor cordless.brbrUnfortunately, we do not accept reservations where payment is intended to come from third parties such as businesses, trust managers, or foundations.

1.5 hours from D.C. - No Bay Bridge - Indoor Pool - Private Beach - Sunsets

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$232.44

Located in Piney Point, enjoy what this 3-bedroom house has to offer. This brilliant property features 4 twin bed and 1 full bed in the cozy bedrooms, along with a bonus office space with a queen bed( air mattress ) With heating, TV internet, WiFi, a washing machine, dryer, and AC available, guests can relax in this serene and enjoyable retreat. It's easy to see why you'll be able to brunwind at our place. Accessible to private beachbrPublic pier for fishing, crabbing close by

Charming 3 bedroom house in lovely Piney Point with WiFi, AC

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(14)

$1360.0

Summary:brbrBeach Club, nestled in the Caribbean shores of Piney Point Maryland, guarantees guests an unforgettable resort style experience. As part of the Durham-Hythe Experience collection of homes, Beach Club guests can select from an array of elevated experiences that will ensure everlasting memories. Experience the sand between your toes and sunset cocktails on your own private piece of paradise without the jetlag.brbrbrbrAsk about our Elevated Experiences, including Massages and Chef Services!brbrbrbrThe Space:brbrBeach Club offers 7 bedrooms (6 with ensuite bathrooms), large kitchen and island for 6 people, breakfast nook, decorative fireplaces, 22-seat beach facing dining table, lounge, billiards room, cabin, veranda, beach facing balcony, deck, outdoor grill, outdoor 10-seat dining table, fire-pit, sauna, treatment room, gym. On top of all of this add a 12-seat movie theater and a club house with bar and games exclusively for your use!brbrbrbrGuest Access:brbrBeach Club guests have complimentary access to bikes and kayaks.brbrbrbrOther Things to Note:brbrPlease note that due to insurance and county guidelines a property specific rental agreement will have to be completed prior to your stay. We welcome dogs but do ask that they remain off furniture and beds. A maximum of three pets are allowed. We also have a pet fee of $50 per pet, per night. We allow events on a case-by-case basis and charge additional fees for these ($100 per guest over 14th guest at any time per day).

Beach Club: your own private Caribbean resort

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$559.25

Summary:brbr**Welcome to Cove Cottage!**brbrbrbrEscape to our charming cottage on the tranquil shores of Piney Point Waters. Enjoy stunning views and the soothing sounds of nature in this unique retreat, perfect for couples, families, or solo travelers. Our cozy space features modern amenities (sauna, hot tub, fire-pit, Wi-Fi, arcade, and kayaks). Spend your days exploring nearby trails on our bicycles or relaxing on the deck swings. Book your stay today and discover the ideal spot to unwind in nature’s beauty!brbrbrbrThe Space:brbrPiney Point, MdbrbrbrbrGuest Access:brbrWhole property!brbrbrbrOther Things to Note:brbrWe will send you a unique access code one hour before your scheduled check-in.brbrbrbrDogs (max two) are welcome for a fee of $50 per dog per night. Please ensure pets are kept off furniture and beds. Violations of these rules will incur additional fees and/or penalties.brbrbrbrPlease note that due to insurance and county guidelines, a property-specific rental agreement will have to be completed prior to your stay.

Cove Cottage

Piney Point, Maryland, United States

Bath

Sleeps

Exceptional(4)

$385.21

Welcome to your dream getaway in charming Piney Point, nestled in historic St. Mary’s County. This beautifully maintained 3-level waterfront home offers the perfect blend of serenity, luxury, and adventure, all in one unforgettable stay.brbrWake up to sweeping water views from nearly every room. This spacious retreat features a private pier, complete with a ladder, floating dock for jet skis—perfect for boating, kayaking, paddleboarding, crabbing, or just soaking in the peaceful surroundings! 3 kayaks available for your use. Life jackets and paddles provided. brbrThe open floor plan of this 3-bedroom, 3.5-bath home is designed for comfort and elegance. Enjoy breathtaking water views from almost every room in this expansive residence. House features include the resurfaced pier, dual HVAC systems, and a whole-house dehumidifier, ensuring year-round comfort. brbrThe ground level presents a versatile space with a full bathroom, pull-out queen sofa bed, 65” wall mounted TV, sink with counter space/cabinets. Step through the sliding door to a covered paver patio w/ outdoor gas fireplace, leading to the fenced-in backyard and your private 100 ft pier. Whether you're boating, jet skiing, kayaking, paddleboarding, swimming, crabbing or fishing, this serene setting promises endless relaxation and enjoyment. brbrOn the second level, you'll find a gourmet kitchen with an island w/ seating, a 6 person dining room table, a walk-in pantry, stylish tile backsplash w/under cabinet lighting. The kitchen is equipped with necessary appliances, utensils, cooking pots/pans, toaster, air fryer, blender, and outdoor grill. brbrThe family room is highlighted by a tiled gas fireplace, a 65” wall mounted TV, a walk-out large deck w/ a 6 person outdoor table, 2 person sitting area, powder room, and magnificent views of the protected St. George Harbor. brbrRetreat to the upper floor where the two guest bedrooms offer comfortable bedding and closet organizers for ample storage. The luxurious primary bedroom features a walk-in closet, a private balcony with a ceiling fan; perfect for enjoying your morning coffee while overlooking the harbor. The attached primary bathroom offers a walk-in shower, double sinks, and basic amenities. brbrYou’re free to fully embrace the waterfront lifestyle. ALL THIS is conveniently located just miles from boat ramps/slips, marinas w/ dry docking, fishing piers, chartered boats, state parks, canoe rentals, campgrounds & picnic areas, historic museums & lighthouse, and a variety of dining and shopping options. Plus, you're only 20 miles from the vibrant Solomon’s Island, 13 miles from Pax River NAVAIR, and about 1.5 - 2 hours from Washington, D. C. , and Annapolis, MD. This property is a RARE gem, meticulously cared for, and ready to become your weekend getaway retreat.

Charming Waterfront 3-bedroom house in Piney Point

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$145.69

Come and relax at The Beach Hive Cottage! Approximately 70 miles from Washington D.C., 14 miles from Patuxent River Naval Air Station, and 16 miles from Saint Mary's College. This beach cottage can sleep up to 7 guests (1 Queen, 2 full, and 1 twin bed). This cottage features everything you need from a fully stocked kitchen, cozy living room, and private bedrooms. It also features a front porch for sipping coffee and a screened back porch for evening cocktails. Water access is just a few minutes walk from the front porch. Enjoy dinner and drinks at Ruddy Duck Seafood house or famous stuffed ham from Chiefs Restaurant. There is a boat ramp within 1 mile of the cottage where you can put your boat/jet ski in the Potomac River or do some recreational fishing!

2 Bedroom Cozy Beach Cottage with Water Access

Piney Point, Maryland, United States

Bed

Bath

Sleeps

Most popular vacation rentals in Piney Point

$169.79

Apartment

Tiny, Funky, and Full of Love - Welcome to the Love Shack

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$218.63

Apartment

Charming waterfront studio with amazing view, and WiFi in tranquil Piney Point

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$247.49

Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$385.21

Charming Waterfront 3-bedroom house in Piney Point

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$559.25

Cove Cottage

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$606.59

WATERFRONT 3000 SQFT HOME W/ PIER, WRAP PORCH, KAYAK, PADDLE BOARD, FIRE PIT

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$640.90

1.5 hours from D.C. - No Bay Bridge - Indoor Pool - Private Beach - Sunsets

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$997.23

Stunning luxury waterfront beach house 90 minutes from the Nations Capital.

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$1360.00

Beach Club: your own private \"Caribbean\" resort

Piney Point, Maryland, United States

Bed

Bath

Sleeps

$201.17