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Vacation rentals in Hollywood

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Top-rated vacation rentals in Hollywood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Rental unit in California

4.92 out of 5 average rating, 200 reviews

Our Little Piece of Heaven

Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Guest suite in Lusby

4.99 out of 5 average rating, 323 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!

Rental unit in Lexington Park

4.97 out of 5 average rating, 534 reviews

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

Cabin in Lusby

4.91 out of 5 average rating, 233 reviews

Peaceful Waterfront Retreat on The Bay

This is a serene, waterside cabin with a private dock, nestled on quiet St. Leonard Creek about one hour outside of Washington, DC. You will enjoy a close quarters stay in this rustic studio cabin, and it is the perfect getaway for anyone looking for some peace and quiet. Come on your own to finally get some work done, or bring your family to enjoy the outdoors! We have two kayaks and two canoes. The house is great for up to two couples looking to catch up and explore the surrounding area.

Rental unit in Lexington Park

4.97 out of 5 average rating, 115 reviews

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Loft in Lusby

5 out of 5 average rating, 339 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Rental unit in Leonardtown

4.98 out of 5 average rating, 128 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

Rental unit in Lexington Park

5 out of 5 average rating, 339 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Cottage in California

4.98 out of 5 average rating, 209 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

Tiny home in Solomons

4.95 out of 5 average rating, 583 reviews

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

Home in Lusby

5 out of 5 average rating, 126 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*Heated pool open to 11/11/24* Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-November 11th) with amazing river views.

Cottage in Saint Leonard

4.88 out of 5 average rating, 105 reviews

Spacious Beachfront Retreat w/Dock

Relax with the whole family at this peaceful place to stay. This charming home features 5 bedrooms and 3 full bathrooms. All bedrooms have a waterfront view. Enjoy watersports - kayaking, fishing, paddle boarding; or relax on the beach by a fire and enjoy the sunset. Bring your jet skis or fishing boat, the marina is 5 miles away.

Vacation rentals for every style

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Popular amenities for Hollywood vacation rentals

Free parking on premises

Air conditioning

Stay near Hollywood's top sights

Jefferson Patterson Park & Museum38 locals recommend

Historic Sotterley Plantation27 locals recommend

Perigeaux Vineyards & Winery25 locals recommend

The Front Porch23 locals recommend

Port of Leonardtown Winery23 locals recommend

Veras Restaurant & Marina19 locals recommend

Other great vacation rentals in Hollywood

Guest suite in Lusby

5 out of 5 average rating, 43 reviews

Welcome to Journey's End Hideaway!

Home in Hollywood

4.98 out of 5 average rating, 58 reviews

Waterfront Home: Osprey Getaway

Home in Mechanicsville

5 out of 5 average rating, 63 reviews

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Home in Leonardtown

4.91 out of 5 average rating, 11 reviews

Potomac Fishing & Crab Paradise at Toney's Landing

Guest suite in Lusby

4.96 out of 5 average rating, 57 reviews

Waterfront on St. Leonard Creek at Fort Hill

Home in Montross

4.88 out of 5 average rating, 52 reviews

The Haven at King Copsico - Comfortable and Cozy

Home in Leonardtown

4.9 out of 5 average rating, 29 reviews

Abells Wharf Cottage - Natural Splendor Getaway

Cottage in California

4.89 out of 5 average rating, 18 reviews

Saint Cozy Cottage | waterfront, fire pit, swings

Quick stats about vacation rentals in Hollywood

Total rentals
60 properties
Total number of reviews
2.1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi

Frequently Asked Questions

What are the most popular amenities for Bed And Breakfast Rentals in Hollywood?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Hollywood have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Hollywood. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Hollywood?
Yes! Work meets play with ease at over 30 vacation rentals in Hollywood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do bed and breakfast rentals in Hollywood have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Hollywood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in bed and breakfast rentals in Hollywood?
Experience the best of Hollywood with our bed and breakfast rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Hollywood?
Four-legged friends are welcome in Hollywood. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Hollywood have wifi?
Absolutely! We offer over 30 house rentals with wifi in Hollywood. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Hollywood?
Hollywood has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore