Hollywood holiday homes

We found 143 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Hollywood to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Hollywood

Showing deals for:18 Dec - 25 Dec

Dining
Property grounds
Room
Marina
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
NZ$3,956
for 7 nights, 1 houseboat
NZ$565 per night
includes taxes & fees
Houseboat on Solomons Island
Terrace/patio
Dining
Living area
Exterior
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
NZ$6,846
for 7 nights, 1 home
NZ$978 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Interior
Property grounds
Dining
Exterior
Exceptional
(25 reviews)

Breton Bay Family Getaway

Leonardtown

10% off
NZ$7,813
for 7 nights, 1 home
NZ$1,116 per night
includes taxes & fees
Breton Bay Family Getaway
A quiet and relaxing road with an abundance of deer, birds, squirrels, and crab.
Piney Point Light House and underwater park with German U-Boat is 5 miles away.
A dining room table expands to 12 seats with a view. Two extensions not show.
Property grounds
Exceptional
(66 reviews)

Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset

Tall Timbers

12% off
NZ$3,582
for 7 nights, 1 cottage
NZ$512 per night
includes taxes & fees
Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset
Property grounds
Exterior
Dining
Property grounds
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
NZ$9,965
for 7 nights, 1 home
NZ$1,424 per night
includes taxes & fees
Magnificent Water Front Property
A wall of windows in main living area offers stunning panoramic Potomac views.
Deck view at dusk.
Looking from kitchen and dining room to the primary bedroom.
Dining room
Exceptional
(17 reviews)

Water's Edge Cottage -- Luxury Retreat -- 180 Degree Potomac Views

Leonardtown

8% off
NZ$5,245
for 7 nights, 1 home
NZ$749 per night
includes taxes & fees
Water's Edge Cottage -- Luxury Retreat -- 180 Degree Potomac Views
Room
Property grounds
Beach
Miscellaneous
Wonderful
(15 reviews)

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict

8% off
NZ$2,763
for 7 nights, 1 cottage
NZ$395 per night
includes taxes & fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
steps to the loft
entryway
dining area
loft bedroom
Exceptional
(61 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
NZ$2,260
for 7 nights, 1 cottage
NZ$323 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(174 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
NZ$2,534
for 7 nights, 1 cottage
NZ$362 per night
includes taxes & fees
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Partial view of the water
Hilltop cottage December
Wiew out east side windows
Open floor plan, dining table and sleep sofa
Exceptional
(30 reviews)

Quiet Woodland cottage near St. Leonard's Creek

Lusby

8% off
NZ$1,773
for 7 nights, 1 cottage
NZ$253 per night
includes taxes & fees
Quiet Woodland cottage near St. Leonard's Creek
Side view
Coffee, tea, cream, and sugar provided
Living room
Front porch
Exceptional
(16 reviews)

Two bedroom two bath home on charming Solomons Island

Solomons

8% off
NZ$4,244
for 7 nights, 1 apartment
NZ$606 per night
includes taxes & fees
Two bedroom two bath home on charming Solomons Island
Private kitchen
Living area
View of parking pad 1 car is backed in and 1 for studio on the bay pulled in.
Exterior detail
Exceptional
(31 reviews)

Studio on the Bay.

St. Leonard

8% off
NZ$2,110
for 7 nights, 1 apartment
NZ$301 per night
includes taxes & fees
Studio on the Bay.
Living area
View from driveway
Interior
Kitchen is stocked with pots pans, dishes etc
Exceptional
(17 reviews)

Solomons Island with views of harbor!

Solomons

8% off
NZ$2,610
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
Solomons Island with views of harbor!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting historical Hollywood

Enjoy the history and other features of Hollywood. Renowned for its restaurants, sporting events and shopping, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Hollywood

Are you searching for things to do in the area? Venture out of your holiday home and check out everything that makes Hollywood a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Running Hare Vineyard (10.8 mi / 17.4 km)
  • Michael P. O'Brien Athletics and Recreation Center (14.2 mi / 22.8 km)
  • Maryland International Raceway (14.4 mi / 23.1 km)
  • Budds Creek Motocross Park (14.6 mi / 23.5 km)
  • Breton Bay Golf Course (8.1 mi / 13 km)
  • Wicomico Shores Golf Course (15.2 mi / 24.4 km)

Exploring the natural landscape of Hollywood

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Hollywood. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • St. Mary's River State Park (6.8 mi / 11 km)
  • Flag Ponds Nature Park (8.7 mi / 13.9 km)
  • Matoaka Beach (9.2 mi / 14.9 km)
  • Cove Point Beach (10.1 mi / 16.3 km)
  • St. Clement's Island State Park (13.7 mi / 22.1 km)
  • Piney Point Beach (15.4 mi / 24.7 km)

Transport options to and around Hollywood

Fly into Ronald Reagan National Airport (DCA), the closest airport, located 42.3 mi (68.1 km) from the city centre.

Frequently asked questions

What is the best area to stay in Hollywood when booking a holiday rental?
When considering a holiday rental in Hollywood, Maryland, the area around the waterfront offers a delightful experience for visitors. This picturesque neighbourhood is known for its serene environment and proximity to the Patuxent River, making it ideal for those who enjoy outdoor activities like fishing and kayaking.One of the top attractions in this area is the Hollywood Farmers Market, which showcases local produce and crafts, providing a charming atmosphere for visitors to immerse themselves in the community. Additionally, the nearby St. Mary's County Museum Division offers rich insights into the region's history and culture, making it a worthwhile visit.In terms of holiday rentals, the waterfront area features a range of properties, from cosy cottages to spacious homes, ensuring there are options to suit various preferences and budgets.
Where are the best areas for renting a beach house in Hollywood?
For renting a beach house in Hollywood, Maryland, the area near the Hollywood Beach offers a picturesque setting with direct access to the sandy shores of the Chesapeake Bay. Properties in this vicinity often come with amenities such as spacious outdoor decks, private beach access, and fully equipped kitchens, which are superb for families or groups looking to enjoy a seaside getaway. Many beach houses boast stunning views of the bay and are designed with comfortable living spaces to enhance the holiday experience.Additionally, the nearby St. Mary's River State Park presents an excellent opportunity for nature lovers, with trails for hiking and scenic spots for picnicking. Rentals in this area frequently feature backyard spaces for barbecues and gatherings, making them ideal for enjoying warm summer evenings under the stars. The local atmosphere is relaxed, with access to charming shops and eateries in the nearby town, providing convenience for beachgoers.
What is the most popular type of holiday rental accomodation in Hollywood?
In Hollywood, Maryland, holiday houses are a popular choice among travellers, with several available in the area. These homes typically provide ample space, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas such as decks or gardens, making them ideal for families or groups seeking a comfortable retreat. Additionally, there are several apartments in the vicinity, which offer a more compact and convenient accommodation option. These apartments usually come with modern amenities, including kitchen facilities and living areas, superb for couples or small families looking for a cosy stay.
Are there any family house rentals in Hollywood?
In Hollywood, Maryland, there are several family-friendly house rentals available, making it a lovely spot for those travelling with children. The area offers spacious homes that often feature amenities such as fully equipped kitchens, ample living areas for family gatherings, and outdoor spaces for kids to enjoy. Some properties may even include features like private decks or backyards, superb for barbecues and relaxation.Visitors can explore nearby attractions, including the beautiful beaches of the Chesapeake Bay and the serene parks that dot the landscape. The local community also boasts charming shops and restaurants, providing convenient options for family outings.
Are there any remote work holiday rentals in Hollywood?
In Hollywood, Maryland, there are several remote work holiday rentals available, with around 12 options to choose from. The area offers a tranquil environment, superb for those looking to balance work and leisure. Many properties come equipped with essential remote work amenities, including high-speed internet, Wi-Fi in rooms, and dedicated workspaces featuring desks and computer monitors.The scenic surroundings provide opportunities for relaxation after work, with beautiful views and access to local attractions such as parks and waterfront areas. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Hollywood?
In Hollywood, popular holiday rental amenities include essential features that cater to the needs of travellers. Most rentals come equipped with kitchens, allowing guests to prepare their own meals, and coffee and tea makers for that morning boost. Onsite parking is also a key amenity, providing convenience for those travelling by car. Additionally, many properties offer travel cribs, making them family-friendly for those with young children, as well as blenders for those who enjoy smoothies or preparing fresh drinks.
When is the best time to visit Hollywood for a holiday rental?
The best time to visit Hollywood, Maryland, for a holiday rental is during the peak season from July to September. This vibrant period draws visitors who are keen to enjoy the warm weather, beautiful waterfront views, and engaging outdoor activities. July stands out as the most popular month, where families and friends come together to relish the summer sunshine, making it an ideal time for swimming, kayaking, and enjoying the local parks.During these months, temperatures typically range from 20 to 30 degrees Celsius, providing a comfortable climate for exploring the charming streets of Hollywood and its scenic surroundings. You'll find that the area is bustling with various events and festivals, offering an authentic taste of local culture and community spirit.For those looking to save a bit on their holiday rental, December can be a more budget-friendly option. During this time, the holiday season brings a unique charm to Hollywood, with festive decorations and a peaceful atmosphere superb for a relaxing getaway.
What are the top attractions in Hollywood?
In Hollywood, Maryland, visitors can enjoy a variety of attractions that showcase the area's natural beauty and charm. One of the main draws is the picturesque St. Mary's River, where outdoor enthusiasts can enjoy activities like kayaking and fishing. The nearby Point Lookout State Park offers scenic views of the Chesapeake Bay and has a rich history, with remnants of a Civil War fort and beautiful hiking trails.For those interested in local culture, the Historic St. Mary's City is a fascinating destination, featuring a living history museum that highlights the early historic period of Maryland. Visitors can explore reconstructed buildings and interact with staff in period costume.The area also boasts several quaint waterfront restaurants and shops, particularly along the scenic roads, providing a superb backdrop for a relaxing day out.
Are all fees included in the Hollywood holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Hollywood holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Hollywood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Hollywood holiday homes?
You can find great discounts on holiday homes in Hollywood on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Hollywood holiday home booking on Bookabach?
To find Hollywood holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Hollywood?
A long-stay holiday home in Hollywood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Hollywood holiday home?
Book your Hollywood holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Hollywood?
Prices for holiday homes in Hollywood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Hollywood to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.