House vacation rentals in Hollywood

4.99 out of 5 average rating, 113 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!

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, 120 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, 186 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.

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

3+N PROMO Waterfront + Gameroom | Dogs + EV OK

*Ask about our 3+ Night promotions* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨‍🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK 🎯 Gameroom ⚡️EV Outlet If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! Book your getaway today or ❤️ us for next time!

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, 102 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!

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

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

5 out of 5 average rating, 135 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, 188 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.

4.98 out of 5 average rating, 121 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.

Popular amenities for Hollywood house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 32 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

4.96 out of 5 average rating, 24 reviews

The living room features three couches arranged around a glass coffee table, providing ample seating. A television is positioned for viewing, with light streaming through the large windows dressed with curtains. The warm tones of the wooden floors and brick wall create a cozy atmosphere.

Home in Charlotte Hall

Cozy Retreat w/ Pool: MIR & DC

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 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 living area features a modern television displaying a serene coastal scene. A light wooden cabinet with woven detailing is positioned beneath the screen. A round coffee table with a metallic finish sits in the center, accompanied by a decorative bowl and literature.

5 out of 5 average rating, 12 reviews

Bliss By The Bay Chalet

Superhost

An aerial view captures the property's layout on a wooded peninsula, surrounded by water on three sides. The main house and guest house are visible amidst the greenery, with a dock extending into the cove, highlighting the peaceful and secluded setting.

5 out of 5 average rating, 3 reviews

Spacious Private Retreat on the Patuxent River

4.96 out of 5 average rating, 27 reviews

The exterior of the home is showcased, featuring a classic white facade with two columns supporting the upper porch. A landscaped yard with colorful foliage and stones frames the outdoor seating area, which includes chairs and decorations. Natural light highlights the inviting entrance.

Home in California

Waterfront, pier, hot tub, pool, pizza oven

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.

4.96 out of 5 average rating, 23 reviews

Creekside Oasis

4.97 out of 5 average rating, 29 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

4.97 out of 5 average rating, 67 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, 36 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

4.93 out of 5 average rating, 60 reviews

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

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!

Superhost

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

4.8 out of 5 average rating, 61 reviews

2 Bedroom Cozy Beach Cottage

5 out of 5 average rating, 37 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

Private house rentals

A wooden dock extends into calm waters, framed by lush greenery. The two-story house stands in the background, featuring a spacious deck with outdoor seating. Pathway lights line the sides of the dock, guiding the way for evening strolls along the waterfront.

4.9 out of 5 average rating, 10 reviews

Waterfront home on Mill Creek-5BR-Hot tub & Kayaks

4.93 out of 5 average rating, 30 reviews

A bright living area features large windows that allow natural light to fill the space. Two comfortable sofas are positioned near a patterned area rug. A round coffee table and a small accent table provide surface space, complemented by soft drapes framing the windows.

Home in Prince Frederick

Chesapeake Escape

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.

4.82 out of 5 average rating, 17 reviews

Waterfront! The River's Roost on the Patuxent!

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!

A spacious living area is featured, showcasing a floral-patterned sofa and a glass coffee table. Decorative elements such as potted plants and an ornate display cabinet with collectibles create a homey environment. Natural light fills the space from large windows, enhancing the warm tones of the decor.

4.83 out of 5 average rating, 58 reviews

Waterfront home with three bedrooms,3 full baths

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.

5 out of 5 average rating, 17 reviews

Driftwood Haven, Chesapeake Bay views throughout

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.