House vacation rentals in Hollywood

4.97 out of 5 average rating, 153 reviews

A two-story farmhouse with a light blue exterior features white trim and is complemented by a welcoming front porch. Rocking chairs are positioned on the porch, surrounded by colorful flower beds and lush green grass. Mature trees provide partial shade, enhancing the outdoor setting.

Home in Church Creek

Church Creek Charm (close to Blackwater Refuge)

Charming Eastern Shore home built in 1900, located in CHURCH CREEK, MD, less than 10-15 mins from Cambridge, Blackwater National Wildlife Refuge & the Harriet Tubman Underground Railroad museum. Ideal spot for cycling, birding, fishing, canoeing, relaxing, or exploring the many cute towns of Maryland's Eastern Shore. Just over an hour from Ocean City & Assateague Nat'l Seashore. Pet-friendly with a fenced backyard. The Eastern Shore is famous for its seafood, history, nature & fresh produce!

A bright living area is illuminated by large windows, providing a view of the surrounding greenery. A comfortable sectional sofa is arranged around a centerpiece coffee table, while a small pool table sits nearby. Natural light enhances the airy atmosphere of the room.

4.9 out of 5 average rating, 105 reviews

SoMD Waffle House 1.5 acres of cozy coastal living

Welcome to our Southern MD beach house. This 3 bedroom and 2 bath home is situated on nearly 1.5 acres of property where you can breathe deep and take in the bay breeze. Whether it is visiting one of the Chesapeake Bay beaches only a 3 minute drive from the home, or watching for wildlife in our yard (it is common to see deer, rabbits, birds, etc), life in Calvert County will slow you down and help you take a much needed break from the daily grind. And you don't even have to cross the Bay Bridge!

4.99 out of 5 average rating, 116 reviews

An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.

Home in North Highland

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.

4.95 out of 5 average rating, 123 reviews

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.

4.98 out of 5 average rating, 237 reviews

Cove Point Cottage with Chesapeake Bay views

Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

5 out of 5 average rating, 119 reviews

The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.

Home in Solomons

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

5 out of 5 average rating, 137 reviews

A single-story house is shown with blue siding and white trim, featuring a prominent brick chimney and a welcoming pink door. Large windows provide ample natural light. A grassy area surrounds the home, with trees adding greenery in the background.

Home in Piney Point

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

4.89 out of 5 average rating, 151 reviews

A stone pathway leads to a two-story house with white siding and turquoise accents. A fenced yard features a well-maintained lawn. The entrance is adorned with a porch that includes two chairs, providing a welcoming space for relaxation. Overhead, the sky presents a mix of clouds.

Home in Solomons

Perfect spot for a Vacay!

Be an Islander! This incredibly well-positioned home has 6-car parking and views of the Patuxent River and Solomons Island. Enjoy year-round life on the water. This is the dream vacation spot with so much to offer. Watch fireworks, fish, crab, enjoy beautiful sunrises & sunsets from the private pier or while relaxing in the gazebo. The local marina, shops, bars, and restaurants are within walking distance. Enjoy the best seafood Southern Maryland has to offer, a crab cake to die for!

4.92 out of 5 average rating, 190 reviews

The exterior of the house showcases multiple large windows that invite natural light, with a spacious porch area featuring white outdoor chairs. Colorful flower planters enhance the surroundings, providing a serene setting among greenery.

Home in Saint Leonard

Cozy Cottage on the Chesapeake Bay

Tranquility supreme. Sit on the terrace and gaze at the Chesapeake Bay. Sandy beach -- just 50 steps from front door; quiet residential area; nearby antiquing & fishing; Only 75 min. from DC. Finish your book or just replenish your spirit. Enjoy. Oh, one more thing — looking for the perfect place for a retreat for your small DC team? Strategic planning will be even more creative and enjoyable when you have the Chesapeake Bay as your muse. Note: This property is for non-smokers.

4.98 out of 5 average rating, 126 reviews

A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.

Home in Dameron

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

The exterior of a renovated beach house is depicted, featuring a wide entrance with steps leading to a spacious deck. The deck is furnished with a dining set and a shaded lounge area, while greenery surrounds the property, enhancing its tranquil setting.

5 out of 5 average rating, 213 reviews

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

A bright sun porch features a round glass dining table surrounded by four light-colored chairs. Large windows provide views of the waterfront, allowing natural light to fill the space. A cozy seating area is visible in the background, offering a serene atmosphere.

5 out of 5 average rating, 146 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. Be sure to visit our sister property, Water's Edge Cottage.

Popular amenities for Hollywood house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 10 reviews

An aerial view captures the single-story home situated on a private peninsula, surrounded by water. Lush green lawns and trees frame the property, while a dock extends into the bay. A pool is visible in the backyard, adding to the outdoor amenities.

Home in Abell

New, Waterfront Home w/ Island on St. Clements Bay

A spacious bedroom features a large wooden bed with a light comforter and decorative pillows. Two leather benches are positioned at the foot of the bed. Natural light fills the room through large windows adorned with wooden shades, and a ceiling fan adds to the comfort.

4.98 out of 5 average rating, 132 reviews

3N+ PROMO-Waterfront w/Gamerm, Firepit, Dog+EV OK

A charming riverfront home is framed by lush greenery and colorful flowerpots. A welcoming pathway leads to the front door, flanked by well-maintained garden beds. The expansive porch invites relaxation, with captivating views of the serene landscape visible in the distance.

4.95 out of 5 average rating, 38 reviews

New Private Beachfront panoramic view every window

A covered porch features a spacious deck with comfortable lounge chairs, offering views of the water. Lanterns hang from the ceiling, and a dining space is surrounded by tall trees, creating a relaxing outdoor atmosphere.

4.97 out of 5 average rating, 97 reviews

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks

A private beach area is depicted with soft, sandy ground, featuring two beach chairs under a blue umbrella. Calm waters extend to the horizon, complemented by a wooden dock and a distant view of the opposite shore under a clear, blue sky.

4.92 out of 5 average rating, 224 reviews

The Glebe

4.97 out of 5 average rating, 127 reviews

An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.

Home in Cambridge

Gorgeous, Waterfront Home Is Fabulous in Winter!

A tranquil view of the private pool framed by potted plants featuring colorful flowers. The pool area extends towards a serene body of water, surrounded by trees. The distant shore is visible, enhancing the natural beauty of the setting.

5 out of 5 average rating, 33 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

4.92 out of 5 average rating, 90 reviews

Spacious and private waterfront, sleeps 10

Weekly house rentals

5 out of 5 average rating, 51 reviews

A private balcony extends from the studio, offering seating for relaxation. Breathtaking waterfront views of the serene landscape and grassy shoreline are visible beyond the railings, surrounded by trees that add a natural touch to the outdoor space.

Home in Piney Point

Waterfront Studio | Bikes & Kayaks | Beach Access

A peaceful waterfront scene is depicted, featuring chairs arranged on a grassy area. A picnic table and a flagpole stand nearby, while the sun reflects on the calm water. A private pier extends into the river, creating a serene atmosphere.

4.97 out of 5 average rating, 29 reviews

Potomac Fishing & Crab Paradise at Toney's Landing

4.97 out of 5 average rating, 39 reviews

Two white Adirondack chairs are placed on a grassy area, facing a calm body of water. A sliver of rainbow is visible in the sky above the horizon. Lush greenery surrounds the scene, with a large tree providing shade.

Home in Chesapeake Beach

Mid-Century Modern: Direct Private Beach Access

A serene waterfront view captures the calm waters of the Potomac River at dusk. Pink and orange hues are reflected on the surface, with a wooden dock extending into the water. The shoreline is lined with smooth stones and grassy areas, framed by trees in the background.

4.92 out of 5 average rating, 95 reviews

The Haven at King Copsico Comfortable, Clean, Cozy

The exterior of the Manor features a brick facade complemented by a green metal roof. A welcoming front door is set under an archway. Natural landscaping surrounds the entryway, with a path leading to the entrance and a shaded area provided by a large tree.

5 out of 5 average rating, 22 reviews

Historic Manor - Main House

5 out of 5 average rating, 91 reviews

A cozy living area is highlighted by a sleek gas fireplace built into textured stone. Decorative plants and vases with yellow flowers add a touch of color to the space. A dark seating arrangement invites relaxation, complemented by a decorative side table and soft lighting.

Home in Waldorf

Spacious Studio Apartment with private entrance

A spacious parking area is visible in front of a single-story house, surrounded by large trees. The building features a welcoming porch and two garage doors. An expansive blue sky complements the serene outdoor setting.

4.84 out of 5 average rating, 19 reviews

Garden Getaway

4.94 out of 5 average rating, 85 reviews

A sandy pathway leads through coastal vegetation to a serene beach scene, where umbrellas in bright yellow and red dot the shoreline. Beachgoers can be seen enjoying the water under a clear blue sky, framed by distant clouds far on the horizon.

Home in Saint Leonard

Cottage on the Bay

Private house rentals

5 out of 5 average rating, 12 reviews

Home in La Plata

* NEW 8-25-25 * - All Private, One Bedrm Apartment

4.95 out of 5 average rating, 81 reviews

An open-concept living area features a kitchen island with a sink, paired with white cabinetry and granite countertops. A dining table made of natural wood is prominently displayed, while a cozy seating area with light-colored sofas and a brick fireplace is visible in the background.

Home in Newburg

Beautiful, serene waterfront property

A window frame is visible, showcasing a scenic view of the Potomac River. A telescope is positioned within the frame, aimed towards the tranquil waters. The horizon features trees and a distant shoreline, while a wooden fence adds a touch of structure to the foreground.

4.86 out of 5 average rating, 70 reviews

Potomac River Getaway

A spacious wooden deck is showcased, extending from the house and featuring several outdoor chairs arranged around a table. The sun sets in the background, casting a warm glow over the grassy yard and the nearby water, enhancing the serene ambiance.

4.95 out of 5 average rating, 82 reviews

The River House: A private waterfront oasis…

5 out of 5 average rating, 38 reviews

Home in Madison

Madison Bay Club House

4.98 out of 5 average rating, 43 reviews

The exterior of a spacious home is showcased, featuring a wraparound deck that invites outdoor living. Large windows reflect natural light, and a turret structure rises above the roofline, surrounded by lush green trees and a well-maintained lawn.

Home in Solomons

4-BR Unique Waterfront House - Your Perfect Escape

Superhost

A hot tub is set within a private deck area, surrounded by lush greenery. Soft lighting creates a warm ambiance as steam rises gently from the water, and a scenic view of trees can be seen in the background at twilight.

Home in Colonial Beach

4.87 out of 5 average rating, 86 reviews

The Lake Oasis Retreat *cozy, serene, relaxing*

A private dock extends over calm waters, providing access to the waterfront oasis. Surrounding trees display vibrant autumn colors, reflecting in the water, while a covered area at the end of the dock offers a spot for relaxation. The serene landscape invites tranquility.