House vacation rentals in Hollywood

5 out of 5 average rating, 159 reviews

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.

4.98 out of 5 average rating, 101 reviews

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

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, 119 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.

4.99 out of 5 average rating, 185 reviews

A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.

Home in Cambridge

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

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, 232 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, 109 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.

4.99 out of 5 average rating, 101 reviews

A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.

Home in Leonardtown

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

5 out of 5 average rating, 133 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

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.

4.92 out of 5 average rating, 186 reviews

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.

5 out of 5 average rating, 123 reviews

A contemporary cottage rests by tranquil water, surrounded by trees. A spacious deck with white railings adjoins the home, leading down to the water’s edge. A small blue kayak is positioned nearby, complementing the serene landscape reflected in the water.

Home in Colonial Beach

Waterfront Cottage in Colonial Beach at Placid Bay

Luxury Cottage with private water views full of natural wildlife. You will love the open floor plan with a chef's kitchen stocked with All the essentials including beverages and coffee. Sleep late with private bedrooms that include luxurious bedding Enjoy the expansive outdoor space complete with Patio, Pergola, Fire Pit, and large deck with outdoor kitchen. Walk down to the 28ft foot dock where you can fish, relax in the sun or take the Kayaks for a ride Close to DC and NOVA

4.98 out of 5 average rating, 120 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, 209 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.

Popular amenities for Hollywood house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 123 reviews

3N+ PROMO Waterfront | Gamerm+Firepit | Dog+EV OK

4.99 out of 5 average rating, 130 reviews

A spacious waterfront home is showcased, featuring a large porch and neatly manicured lawns. The property includes a sandy beach leading to the calm waters of Fishing Creek, with a picturesque background of trees and a second building in the distance.

Home in Woolford

Starboard on McKeil Point, w/heated pool & hot tub

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.

4.97 out of 5 average rating, 31 reviews

New Private Beachfront panoramic view every window

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, 222 reviews

The Glebe

4.97 out of 5 average rating, 31 reviews

The exterior of the house is showcased, featuring a front stone chimney and a welcoming turquoise door. A spacious lawn surrounds the property, with a driveway visible to the right. Trees are seen in the background, highlighting the peaceful neighborhood setting.

Home in Colonial Beach

Stay&Play:Games, Pool, FirePit, Beach & Boardwalk!

A wooden dock extends over calm waters, bordered by tall trees displaying autumn colors. The surface of the water reflects the surrounding scenery, creating a serene atmosphere. Soft fog hovers above the water, enhancing the peacefulness of the natural setting.

4.92 out of 5 average rating, 87 reviews

Spacious and private waterfront, sleeps 10

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

A wooden dock extends toward a tranquil waterway, framed by tall grass and a colorful sunset. The sky features hues of orange and purple, reflecting on the water's surface. The scene invites relaxation and appreciation of nature's beauty.

4.98 out of 5 average rating, 169 reviews

Beach Please! River cottage w/private beach & dock

Weekly house rentals

A well-maintained backyard features expansive grassy areas bordered by trees, providing natural shade. A wooden deck extends from the house, furnished with outdoor seating. A stone retaining wall defines the space, enhancing the inviting atmosphere of the outdoor area.

4.95 out of 5 average rating, 22 reviews

Creekside Oasis

5 out of 5 average rating, 43 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

4.97 out of 5 average rating, 66 reviews

A spacious living area is framed by tall windows that provide views of the outdoor greenery. The high wooden ceiling features exposed beams, and natural light enhances the inviting atmosphere. A cozy sofa arrangement is visible, along with a patterned area rug on the wooden floor.

Home in Huntingtown

House near Patuxent River

4.97 out of 5 average rating, 35 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 sandy beach area is visible, flanked by gentle waves lapping against the shore. The horizon is marked by a clear blue sky with wispy clouds, creating a serene coastal environment. Lush greenery can be seen in the background, enhancing the natural landscape.

4.9 out of 5 average rating, 71 reviews

Hickory House on the Chesapeake Bay!

4.99 out of 5 average rating, 85 reviews

The exterior of a two-story home features a spacious front porch with white railing. A large arched window is positioned above the entrance. The surrounding area includes a paved driveway and grassy space, with trees providing a natural backdrop.

Home in Solomons

Solomons home with harbor view!

4.92 out of 5 average rating, 38 reviews

A lush green lawn extends towards Breton Bay, bordered by trees and flowering plants. The calm water reflects the sky, with a red gazebo visible in the distance. Gentle hills create a serene backdrop, inviting relaxation and outdoor activities.

Home in Leonardtown

Abells Wharf Cottage - Natural Splendor Getaway

5 out of 5 average rating, 27 reviews

An open living space features large windows framing views of the water. A cozy seating area includes a brown couch, while a kitchen bar offers high chairs. Natural wood beams highlight the ceiling, adding to the inviting ambiance.

Home in Prince Frederick

Downs By The River

Private house rentals

4.96 out of 5 average rating, 24 reviews

The charming exterior of the house features a welcoming front porch with two white rocking chairs and a swing. Lush greenery surrounds the property, complementing the home's light-colored siding and blue shutters. A pathway leads to the front door, enhancing accessibility.

Home in Kinsale

Nature's Retreat

A wooden pier extends over the calm waters, flanked by lush greenery. Small boats are visible moored along the dock. The sky is bright with a few scattered clouds, creating a peaceful atmosphere at the shoreline.

4.86 out of 5 average rating, 65 reviews

Spacious Lakefront Cottage w/ Private Pier

4.96 out of 5 average rating, 28 reviews

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.

Home in Leonardtown

Potomac Fishing & Crab Paradise at Toney's Landing

4.93 out of 5 average rating, 60 reviews

Luxury Family 5BR: GameRm, MovieRm, FirePit, Beach

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.

4.88 out of 5 average rating, 52 reviews

Potomac River Getaway

A fire pit made of stone is surrounded by several wooden Adirondack chairs, set against a backdrop of a vibrant sunset over the water. A dock with boats is visible in the distance, along with a blue shed and a peaceful grassy area.

4.81 out of 5 average rating, 16 reviews

Waterfront! The River's Roost on the Patuxent!

4.8 out of 5 average rating, 61 reviews

A gentle sunset casts warm hues over a serene waterfront scene. The coastline features a lighthouse near a small, two-story building, with a pier extending into the water. Lush greenery surrounds the area, creating a peaceful atmosphere.

Home in Piney Point

2 Bedroom Cozy Beach Cottage

A spacious living area features a long sectional sofa with light-colored fabric, complemented by modern armchairs. Large windows allow natural light and showcase views of the Chesapeake Bay. A sleek fireplace is centered on the grey stone wall, adding warmth to the open space.